Diamine derivatives, process for producing the same, and bactericide containing the same as active ingredient

ABSTRACT

A fungicide can be provided by using, as an active ingredient, a diamine derivative of the following general formula (1):  
                 
wherein R1 to R7 represent a specific substituent such as an alkyl group with 1 to 6 carbon atoms, and R8 represents an aryl group, which may be substituted or a heteroaryl group, which may be substituted.

TECHNICAL FIELD

This invention relates to novel diamine derivatives, a process for producing the diamine derivatives, and a fungicide containing the diamine derivatives as an active ingredient.

BACKGROUND ART

Pest Control plays a significant role in cultivation of paddy rice, and, in particular, various fungicides have been developed and used against rice blast, which is considered to be an important disease injury. These fungicides, however, are not always satisfactory in terms of the desired fungicidal activity and control of the undesirable harmful effects on useful crops. In addition, in recent years, fungi having drug-resistant have emerged due to the frequent use of agricultural and horticultural fungicides, and the existing fungicides do not always exhibit satisfactory fungicidal activity. Furthermore, from the environmental viewpoint, there have been demands for novel fungicides which are safe and capable of controlling harmful fungi at lower concentrations.

DISCLOSURE OF INVENTION

Accordingly, an object of this invention is to provide diamine derivatives, which exhibit excellent effect to control rice blast, but does not injure useful crops.

In order to solve the above-described problems, the present inventors synthesized various novel diamine derivatives and various investigations relating to their fungicidal activities, etc., have been carried out. They have finally found the diamine derivatives, which exhibit excellent effect to control rice blast, but not injure useful crops. As a result the present inventors have completed this invention.

Specifically, this invention include the following embodiments and aspects:

[1] A diamine derivative, represented by the following general formula (1):

wherein

R1 represents an alkyl group with 1 to 6 carbon atoms [provided that the case is excluded where R1 is a tert-butyl], a cycloalkyl group with 3 to 6 carbon atoms, an alkenyl group with 2 to 6 carbon atoms, a cycloalkenyl group with 3 to 6 carbon atoms, an alkynyl group with 2 to 6 carbon atoms, an arylalkyl group which may be substituted, a heteroarylalkyl group which may be substituted, an aryl group which may be substituted, or a heteroaryl group which may be substituted;

-   -   R2 and R7 independently represent a hydrogen atom, an alkyl         group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 6         carbon atoms, an alkenyl group with 2 to 6 carbon atoms, a         cycloalkenyl group with 3 to 6 carbon atoms, an alkynyl group         with 2 to 6 carbon atoms, an arylalkyl group which may be         substituted, an aryl group which may be substituted, or an acyl         group;     -   R3 and R4 independently represent a hydrogen atom, an alkyl         group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 6         carbon atoms, an alkenyl group with 2 to 6 carbon atoms, a         cycloalkenyl group with 3 to 6 carbon atoms, an alkynyl group         with 2 to 6 carbon atoms, an arylalkyl group which may be         substituted, a heteroarylalkyl group which may be substituted,         an aryl group which may be substituted or a heteroaryl group         which may be substituted, or a cycloalkyl group with 3 to 6         carbon atoms including an attached carbon atom;     -   R5 and R6 independently represent a hydrogen atom, an alkyl         group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 6         carbon atoms, an alkenyl group with 2 to 6 carbon atoms, a         cycloalkenyl group with 3 to 6 carbon atoms, an alkynyl group         with 2 to 6 carbon atoms, an arylalkyl group which may be         substituted, or an aryl group which may be substituted; provided         that the case is excluded where R3, R4, R5 and R6 all represent         a hydrogen atom or where any one of R3, R4, R5 and R6 represents         a methyl group which may be substituted and the others represent         a hydrogen atom, and     -   R8 represents an aryl group which may be substituted or a         heteroaryl group which may be substituted.

[2] The diamine derivative according to the above section [1], wherein

-   -   R1 represents an alkyl group with 1 to 6 carbon atoms [provided         that the case is excluded where R1 is a tert-butyl], a         cycloalkyl group with 3 to 6 carbon atoms, an alkenyl group with         2 to 6 carbon atoms, an arylalkyl group which may be         substituted, a heteroarylalkyl group which may be substituted,         an aryl group which may be substituted, or a heteroaryl group         which may be substituted;     -   R2 and R7 independently represent a hydrogen atom, an alkyl         group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 6         carbon atoms, an arylalkyl group which may be substituted, an         aryl group which may be substituted, or an acyl group;     -   R3 and R4 independently represent a hydrogen atom, an alkyl         group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 6         carbon atoms, an alkenyl group with 2 to 6 carbon atoms, an         arylalkyl group which may be substituted, a heteroarylalkyl         group which may be substituted, an aryl group which may be         substituted or a heteroaryl group which may be substituted, or a         cycloalkyl group with 3 to 6 carbon atoms including an attached         carbon atom; and     -   R5 and R6 independently represent a hydrogen atom, an alkyl         group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 6         carbon atoms, an arylalkyl group which may be substituted, or an         aryl group which may be substituted; provided that the case is         excluded where R3, R4, R5 and R6 all represent a hydrogen atom         or where any one of R3, R4, R5 and R6 represents a methyl group         which may be substituted and the others represent a hydrogen         atom.

[3] The diamine derivative according to the above section [2], wherein

-   -   R2 and R7 independently represent a hydrogen atom, an alkyl         group with 1 to 6 carbon atoms, or an acyl group;     -   R3 and R4 independently represent a hydrogen atom, an alkyl         group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 6         carbon atoms, an arylalkyl group which maybe substituted, an         aryl group which may be substituted, or a cycloalkyl group with         3 to 6 carbon atoms including an attached carbon atom; and     -   R5 and R6 independently represent a hydrogen atom, an alkyl         group with 1 to 6 carbon atoms, an arylalkyl group which may be         substituted, or an aryl group which may be substituted; provided         that the case is excluded where R3, R4, R5 and R6 all represent         a hydrogen atom or where any one of R3, R4, R5 and R6 represents         a methyl group which may be substituted and the others represent         a hydrogen atom.

[4] The diamine derivative according to the above section [3], wherein R2 and R7 represent a hydrogen atom.

[5] A diamine derivative, represented by the following general formula (9):

-   -   wherein R9 represents an alkyl group with 1 to 6 carbon atoms, a         cycloalkyl group with 3 to 6 carbon atoms, an alkenyl group with         2 to 6 carbon atoms, a cycloalkenyl group with 3 to 6 carbon         atoms, an alkynyl group with 2 to 6 carbon atoms, an arylalkyl         group which may be substituted, a heteroarylalkyl group which         may be substituted, a phenyl group, a phenyl group which is         substituted at the fourth position, or a heteroaryl group which         may be substituted;     -   R10 and R15 independently represent a hydrogen atom, an alkyl         group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 6         carbon atoms, an alkenyl group with 2 to 6 carbon atoms, a         cycloalkenyl group with 3 to 6 carbon atoms, an alkynyl group         with 2 to 6 carbon atoms, an arylalkyl group which may be         substituted, an aryl group which may be substituted, or an acyl         group;     -   One of R11 and R12 represents a methyl group, and the other         represents a hydrogen atom;     -   R13 and R14 represent a hydrogen atom, respectively; and     -   R16 represents a phenyl group, a phenyl group which is         substituted at the fourth position, or a heteroaryl group which         may be substituted.

[6] The diamine derivative according to the above section [5], wherein

-   -   R9 represents an alkyl group with 1 to 6 carbon atoms, a         cycloalkyl group with 3 to 6 carbon atoms, an alkenyl group with         2 to 6 carbon atoms, an arylalkyl group which may be         substituted, a heteroarylalkyl group which may be substituted, a         phenyl group, a phenyl group which is substituted at the fourth         position, or a heteroaryl group which may be substituted; and     -   R10 and R15 represent a hydrogen atom, an alkyl group with 1 to         6 carbon atoms, a cycloalkyl group with 3 to 6 carbon atoms, an         arylalkyl group which may be substituted, an aryl group which         may be substituted, or an acyl group, independently.

[7] The diamine derivative according to the above section [6], wherein R10 and R15 independently represent a hydrogen atom, an alkyl group with 1 to 6 carbon atoms, or an acyl group.

[8] The diamine derivative according to the above section [7], wherein at R10 and R15 represent a hydrogen atom, respectively.

[9] A fungicide, wherein it contains the diamine derivative according to any one of the above sections [1] to [8] as an active ingredient.

[10] A process for producing the diamine derivative according to the above section [1], wherein a compound having the following general formula (2):

wherein

-   -   R1, R2, R3, R4, R5, R6 and R7 represent the same groups as those         of the compounds according to the above section [1],     -   is reacted with a compound having the following general formula         (3):         wherein     -   R8 represents the same group as that of the compound according         to the above section [1], and     -   X represents a leaving group.

[11] A process for producing the diamine derivative according to the above section [1], wherein a compound of the general formula (2) is condensed with a compound having the following general formula (4):

wherein

-   -   R8 represents the same group as that of the compounds according         to the above section [1].

[12] A process for producing the diamine derivative according to the above section [1], wherein a compound having the following general formula (5):

wherein

-   -   R2, R3, R4, R5, R6, R7 and R8 represent the same groups as those         of the compound according to the above section [1],     -   is reacted with a compound having the following general formula         (6):         wherein     -   R1 represents the same group as that of the compound according         to the above section [1], and     -   X represents a leaving group.

[13] A process for producing the diamine derivative according to the above section [5], wherein a compound having the following general formula (10):

wherein

-   -   R9, R10, R11, R12, R13, R14 and R15 represent the same groups as         those of the compounds according to the above section [5],     -   is reacted with a compound having the following general formula         (11):         wherein     -   R16 represents the same group as that of the compound according         to the above section [5], and     -   X represents a leaving group.

[14] A process for producing the diamine derivative according to the above section [5], wherein a compound of the general formula (10) is condensed with a compound having the following general formula (12):

wherein

-   -   R16 represents the same group as that of the compounds according         to the above section [5].

[15] A process for producing the diamine derivative according to the above section 5, wherein a compound having the following general formula (13):

wherein

-   -   R10, R11, R12, R13, R14, R15 and R16 represent the same groups         as those of the compound according to the above section [5],     -   is reacted with a compound having the following general formula         (14):         wherein     -   R9 represents the same group as that of the compound according         to the above section [5], and     -   X represents a leaving group.

BEST MODE FOR CARRYING OUT THE INVENTION

The invention will be described below more in detail.

In the diamine derivatives of the general formulas (1) and (9) and the process for producing the same, examples of the alkyl group with 1 to 6 carbon atoms include methyl, ethyl, propyl, butyl, pentyl, hexyl, allyl, methallyl and propargyl groups; examples of the cycloalkyl group with 3 to 6 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl groups; examples of the alkenyl group with 2 to 6 carbon atoms include vinyl, propenyl, butenyl, pentenyl and hexenyl groups; examples of the cycloalkenyl group with 3 to 6 carbon atoms include cyclopropenyl, cyclobutenyl, cyclopentenyl and cyclohexenyl groups; examples of the alkynyl group with 2 to 6 carbon atoms include ethynyl, propynyl, butynyl, pentynyl and hexynyl groups; examples of the aryl group include phenyl and naphthyl groups; examples of the heteroaryl group include pyridyl, pyrimidyl, thienyl, furanyl, pyrazolyl, imidazolyl, isothiazolyl, isoxazolyl, indolyl, quinolyl, benzofuranyl, benzothienyl, benzoxazolyl, benzoisoxazolyl, benzimidazolyl, benzothiazolyl and benzoisothiazolyl groups; examples of the acyl group include alkylcarbonyl groups such as acetyl group and arylcarbonyl groups such as benzoyl group.

Examples of the substituent(s) of the aryl group and the heteroaryl group include alkyl groups having 1 to 6 carbon atoms such as methyl, ethyl, propyl and butyl groups; cycloalkyl groups having 3 to 6 carbon atoms such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl groups; halogen-substituted alkyl groups having 1 to 4 carbon atoms such as trifluoromethyl, difluoromethyl, bromodifluoromethyl and trifluoroethyl groups; alkoxy groups having 1 to 4 carbon atoms such as methoxy, ethoxy, propoxy and butoxy groups; halogen-substituted alkoxy groups having 1 to 4 carbon atoms such as trifluoromethoxy, difluoromethoxy and trifluoroethoxy groups; alkylthio groups having 1 to 4 carbon atoms such as methylthio, ethylthio, propylthio and butylthio groups; halogen-substituted alkylthio groups having 1 to 4 carbon atoms such as trifluoromethylthio, difluoromethylthio and trifluoroethylthio groups; alkylsulfinyl groups having 1 to 4 carbon atoms such as methanesulfinyl, ethanesulfinyl, propanesulfinyl and butanesulfinyl groups; halogen-substituted alkylsulfinyl groups having 1 to 4 carbon atoms such as trifluoromethanesulfinyl, difluoromethanesulfinyl and trifluoroethanesulfinyl groups; alkyl sulfonyl groups having 1 to 4 carbon atoms such as methanesulfonyl, ethanesulfonyl; propanesulfonyl and butanesulfonyl groups; halogen-substituted alkylsulfonyl groups having 1 to 4 carbon atoms such as trifluoromethanesulfonyl, difluoromethanesulfonyl and trifluoroethanesulfonyl groups, alkylsulfonamide groups having 1 to 4 carbon atoms such as methanesulfonamide, ethanesulfonamide, propanesulfonamide and butanesulfonamide groups; halogen-substituted alkylsulfonamide groups having 1 to 4 carbon atoms such as trifluoromethanesulfonamide, difluoromethanesulfonamide and trifluoroethanesulfonamide groups; halogen atoms such as fluorine, chlorine, bromine and iodine atoms; and acyl groups such as acetyl and benzoyl groups.

The aryl group and the heteroaryl group may be substituted by two or more groups selected from them.

Examples of the methyl group, which may be substituted, include methyl, hydroxymethyl and halomethyl groups.

In the compounds of the general formulas (3), (6), (11) and (14), examples of the leaving groups include halogen atoms such as chlorine atom; alkoxy groups such as methoxy and ethoxy groups; aryloxy groups such as phenoxy group; and imidazole group.

The compounds of the invention represented by the general formulas (1) and (9) are novel. The compounds of formula (1) can be produced by the process shown by the following equation (1):

wherein

-   -   R1, R2, R3, R4, R5, R6 and R7 have the same definitions as those         of the general formula (2), respectively; and     -   R8 and X have the same definitions as those of the general         formula (3), respectively.

In the equation (1), a diamine derivative of the general formula (1) can be produced by reacting a diamine derivative of the general formula (2) or its salt with a well known carbonyl compound of the general formula (3) in a reaction containing either no solvent or a solvent(s), and either in the absence of a base(s) or in the presence of base(s).

Examples of the base used in the reaction shown by the equation (1) include alkaline metal hydroxides such as sodium hydroxide and potassium hydroxide; alkaline earth metal hydroxides such as magnesium hydroxide and calcium hydroxide; alkaline metal hydrides such as sodium hydride and potassium hydride; alkaline metal alcoholates such as sodium methoxide and sodium ethoxide; alkaline metal oxides such as sodium oxide; carbonates such as potassium carbonate and sodium carbonate; phosphates such as tri-potassium phosphate, tri-sodium phosphate, di-potassium hydrogen phosphate, di-sodium hydrogen phosphate; acetates such as sodium acetate and potassium acetate; organic bases such as pyridine, 4-(dimethylamino)pyridine, triethylamine and 1,8-diazabicyclo[5.4.0]undec-7-ene. At least one base can be used in the above reaction.

The quantity of the base(s) is not particularly limited, and when at least one of the above organic bases is used, it can also be used as a solvent.

Examples of the solvent which may be used in the reaction shown by the equation (1) include water; alcohols such as methanol, ethanol, propanol and butanol; halogenated hydrocarbons such as dichloromethane and chloroform; aromatic hydrocarbons such as benzene, toluene and xylene; aliphatic hydrocarbons such as hexane and heptane; polar aprotic solvents such as dimethylformamide (DMF), dimethylacetamide (DMA), dimethyl sulfoxide (DMSO), 1,3-dimethyl-2-imidazolidinone (DMI) and 1-methyl-2-pyrrolidone (NMP); ethers such as diethyl ether, diisopropyl ether, 1,2-dimethoxyethane (DME), tetrahydrofuran (THF) and dioxane; and nitrites such as acetonitrile and propionitrile.

The chemical equivalent of the carbonyl compound of the general formula (3) to the compound of the general formula (2) is preferably 1 to 2, and more preferably 1 to 1.2.

The reaction temperature and reaction time of the above reaction may be changed over a wide range. Generally, the reaction temperature may be preferably in the range from −20 to 200° C., more preferably from 0 to 100° C., and the reaction time may be preferably in the range from 0.01 to 50 hours, more preferably from 0.1 to 15 hours.

The amine derivatives and the salts thereof of the general formula (2) of the equation (1), other than commercially available ones, can be easily produced by the method such as Gabriel's synthesis; Delepine reaction; well known amine synthesis in which cyano group, amide, imine or oxime is reduced; or synthesis described in Tetrahedron Asymmetry, vol. 11, 1907 (2000).

The compounds of the general formula (3) of the equation (1) can be produced by conventional procedures in which a well known derivative of carboxylic acid of the general formula (4) is reacted with thionyl chloride, oxalyl chloride, phosgene or 1,1′-carbonylbis-1H-imidazole.

The compounds of the general formula (3) of the equation (1) can also be produced by conventional procedures in which a well known derivative of carboxylic acid of the general formula (4) is reacted with alcohol such as methyl alcohol or ethyl alcohol without a catalyst or in the presence of a catalyst.

The compounds of the invention, of the general formula (1), can also be produced by the process shown by the following equation (2).

wherein

-   -   R1, R2, R3, R4, R5, R6 and R7 have the same definitions as in         the general formula (2), respectively; and     -   R8 has the same definition as that of the general formula (4).

In the equation (2), a diamine derivative of the general formula (1) can be produced by condensing a diamine derivative of the general formula (2) or its salt with a well known derivative of carboxylic acid of the general formula (4), in a reaction containing no solvent or a solvent(s).

Examples of the condensation agents for this case include:

-   -   N,N′-dicyclohexylcarbodiimide,     -   1,1′-carbonylbis-1H-imidazole,     -   1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride,         2-chloro-1,3-dimethylimidazorium chloride.

As the quantity of the condensation agent to the compound of the general formula (4), the chemical equivalent of the former to the latter is preferably 1 to 2, more preferably 1 to 1.2.

As the organic solvent(s) for this case, the same solvent(s) as those for the process shown by the equation (1) may be used.

Regarding the quantity of the derivative of carboxylic acid of the general formula (4) to the compound of the general formula (2), the chemical equivalent of the former to the latter is preferably 1 to 2, more preferably 1 to 1.2.

The reaction temperature and reaction time of the above reaction may be changed over a wide range. Generally, the reaction temperature may be preferably in the range from −20 to 200° C., more preferably from 0 to 100° C., and the reaction time may be preferably in the range from 0.01 to 50 hours, more preferably from 0.1 to 15 hours.

The compounds of the invention of the general formula (1), can also be produced by the process shown by the following equation (3):

wherein

-   -   R2, R3, R4, R5, R6, R7 and R8 have the same definitions as those         of the general formula (5), respectively; and     -   R1 and X have the same definitions as those of the general         formula (6), respectively.

In the equation (3), a diamine derivative of the general formula (1) can be produced by reacting a diamine derivative of the general formula (5) or its salt with a well known compound of the general formula (6) in a reaction containing no solvent or a solvent(s), either in the absence of a base(s) or in the presence of a base(s).

In this reaction, the same base(s) as those used in the equation (1) can be used.

The quantity of the bases used is not particularly limited, and when the above organic base(s) is used, they can also be used as a solvent.

As the solvent(s) for this case, the same solvent(s) as those used in the process shown by the equation (1) can be used.

Regarding the quantity of the compounds of the general formula (6) to the diamine derivatives of the general formula (5), the chemical equivalent of the former to the latter is preferably 1 to 2, more preferably 1 to 1.2.

The reaction temperature and reaction time of the above reaction may be changed over a wide range. Generally, the reaction temperature may be preferably in the range from −20 to 200° C., more preferably from 0 to 100° C., and the reaction time may be preferably in the range from 0.01 to 50 hours, more preferably from 0.1 to 15 hours.

The compounds of formula (9) can be produced in the same manners by substituting the compounds (2) to (6) in the reaction equations (1) to (3) with the compounds (10) to (14) mentioned above.

There exist asymmetric carbon atoms in the diamine derivatives of the general formulas (1) and (9), depending on the type of substituent(s), and the derivatives can exist as an optical isomer, diastereoisomer, racemic modification or mixture thereof at an arbitrary rate. The invention embraces all isomers of these types and the mixture thereof.

The agricultural and horticultural fungicides containing the diamine derivatives of the invention represented by the general formulas (1) and (9) as an active ingredient exhibit an excellent effect to control rice blast caused by Piricularia oryzae.

The diamine derivatives of the invention of the general formulas (1) and (9) can be used by combining them with at least one of other fungicides, agricultural chemicals such as insecticides, herbicides and plant growth regulators, soil conditioners, and fertilizer responsive substances. They can be applied in the form of a mixture preparation.

Although the diamine derivatives of the present invention may be used as they are, they are preferably used as a formulation in the form of a composition, which can be obtained by mixing them with a carrier including a solid or liquid diluent. The term “carrier” herein used means a synthetic or natural, inorganic or organic materials which is mixed to help the active ingredient reach the target site and make easier the storage, transportation and handling of the active ingredient compounds.

Examples of the solid carriers suitably used in the invention include clays such as montmorillonite, kaolinite and bentonite; inorganic substances such as diatomaceous earth, clay, talc, vermiculite, plaster, calcium carbonate, silica gel and ammonium sulfide; vegetable organic materials such as soybean flour, sawdust and wheat flour; and urea.

Examples of the liquid carriers suitably used in the invention include aromatic hydrocarbons such as toluene, xylene and cumene; paraffin hydrocarbons such as kerosine and mineral oil; halogenated hydrocarbons such as carbon tetrachloride, chloroform and dichloroethane; ketones such as acetone and methyl ethyl ketone; ethers such as dioxane, tetrahydrofuran and diethylene glycol dimethyl ether; alcohols such as methanol, ethanol, propanol and ethylene glycol; dimethylformamide; dimethyl sulfoxide; and water.

In order to enhance the effectiveness of the compounds of the invention, at least one of the following adjuvants can be used solely or in their combination, according to the object, while taking into account the formulation of the compounds, the site of application, etc.

When aiming at emulsification, dispersion, spreading, moistening, binding and stabilization of the compounds, an adjuvant(s) may be used for the formulation. Examples of the adjuvants include anionic surfactants such as ligninsulfonate, alkylbenzenesulfonate, alkylsulfate ester, polyoxyalkylene alkylsulfate ester and polyoxyalkylene alkylphosphate ester; nonionic surfactants such as polyoxyalkylene alkyl ether, polyoxyalkylene alkylaryl ether, polyoxyalkylene alkylamine, polyoxyalkylene alkylamide, polyoxyalkylene alkyl thioether, polyoxyalkylene fatty ester, glycerol fatty ester, sorbitan fatty ester, polyoxyalkylene sorbitan fatty ester and polyoxypropylene polyoxyethylene block copolymer; lubricants such as calcium stearate and wax; stabilizers such as isopropylhydrodiene phosphate; methyl cellulose; carboxymethyl cellulose; casein; and gum arabic. The adjuvants used are not limited to the above described ones.

The quantity of the compounds of the invention as an active ingredient is generally 0.5 to 20% by weight for dust formulation, 5 to 50% by weight for emulsifiable concentrate, 10 to 90% by weight for wettable powder, 0.1 to 20% by weight for granular, and 10 to 90% by weight for flowable. The quantity of carrier in each formulation is generally 60 to 99% by weight for dust, 40 to 95% by weight for emulsifiable concentrate, 10 to 90% by weight for wettable powder, 80 to 99% by weight for granular, and 10 to 90% by weight for flowable, respectively. The quantity of adjuvant is generally 0.1 to 20% by weight for dust, 1 to 20% by weight for emulsifiable concentrate, 0.1 to 20% by weight for wettable powder, 0.1 to 20% by weight for granular, and 0.1 to 20% by weight for flowable.

EXAMPLES

In the following, the invention will be described in further detail taking several examples and test examples.

Example 1 Preparation of N-(methoxycarbonyl)-N′-benzoyl-1-phenyl-1,2-ethylenediamine (Compound No. 66)

0.22 g of benzoyl chloride was added to 10 ml of a solution of 0.25 g of N-(methoxycarbonyl)-1-phenylethylenediamine and 0.2 g of triethylamine in dichloromethane under ice cooling, and the mixture was stirred for 30 minutes at 5° C. and at room temperature for 3 hours. The reaction mixture was rinsed with water, the organic layer was dried over magnesium sulfate anhydrous, and the residual oily material obtained under a reduced pressure was purified by column chromatography on silica gel (2:1 hexane/ethyl acetate) to obtain 0.28 g of the title compound as colorless crystals.

Example 2 Preparation of N-(4-chlorobenzoyl)-N′-(i-propoxycarbonyl)-3-phenyl-1,2-propanediamine (Compound No. 290)

0.21 g of 1,1′-carbonylbis-1H-imidazole was added to a solution of 0.19 g of 4-chlorobenzoic acid in tetrahydrofuran and stirred for 1 hour at room temperature. Then 5 ml of a solution of 0.25 g of 2-(i-propoxycarbonylamino)-3-phenylpropylamine in tetrahydrofuran was added to the above solution and stirred at room temperature for 4 hours. The reaction mixture was rinsed with water, the organic layer was dried over magnesium sulfate anhydrous, and the residual oily material obtained under a reduced pressure was purified by column chromatography on silica gel (2:1 hexane/ethyl acetate) to obtain 0.26 g of the title compound as colorless crystals.

Example 3 Preparation of N-(benzyloxycarbonyl)-N′-benzoyl-1-phenyl-1,2-ethylenediamine (Compound No. 636)

0.12 g of triethylamine was added to 10 ml of a solution of 0.25 g of N-benzoyl-2-phenyl-1,2-ethylenediamine hydrochloride and 0.17 g of benzyl chloroformate in dichloromethane under ice cooling, and the mixture was stirred at 5° C. for 30 minutes and at room temperature for 3 hours. The reaction mixture was rinsed with water, the organic layer was dried over magnesium sulfate anhydrous, and the residual oily material obtained under a reduced pressure was purified by column chromatography on silica gel (2:1 hexane/ethyl acetate) to obtain 0.28 g of the title compound as colorless crystals.

Example 4 Preparation of N-(t-butoxycarbonyl)-N′-(4-methylbenzoyl)-1-phenyl-1,2-ethylenediamine (Compound No. 504)

0.24 g of triethylamine was added to a solution of 0.22 g of di-t-butyl dicarbonate and 0.25 g of N-(4-methylbenzoyl)-2-phenyl-1,2-ethylenediamine hydrochloride in dichloromethane under ice cooling, and the mixture was stirred at 5° C. for 1 hour and at room temperature for 3 hours. The reaction mixture was rinsed with water, the organic layer was dried over magnesium sulfate anhydrous, and the residual oily material obtained under a reduced pressure was purified by column chromatography on silica gel (2:1 hexane/ethyl acetate) to obtain 0.24 g of the title compound as colorless crystals.

The compounds of the general formulas (1) and (9) which can be produced in the same manner as in Examples 1 to 4 are shown in Table 1 below. And the physical properties of some of the compounds are shown in Table 2. R17 to R24 in Table 1 are the substitutions shown in the following formula (15):

In Table 1, Me represents a methyl group, Et represents an ethyl group, n-Pr represents a normal propyl group, i-Pr represents an isopropyl group, i-Bu represents an isobutyl group, s-Bu represents a secondary butyl group, t-Bu represents a tertiary butyl group, Ph represents a phenyl group, Bn represents a benzyl group, 1-Naph represents a 1-naphtyl group, 2-Naph represents a 2-naphtyl group, c-Pr represents a cyclopropyl group, c-Hex represents a cyclohexyl group, Ac represents an acetyl group, Bz represents a benzoyl group, vinyl represents an ethenyl group, allyl represents a 2-propenyl group, propargyl represents a 2-propynyl group, neopentyl represents a 2,2-dimethylpropyl group, methallyl represents a 2-methyl-2-propenyl group, and 2-thienyl represents a thiophene-2-yl group. TABLE 1 Comp. No. R17 R18 R19 R20 R21 R22 R23 R24 1 Me H Me H H H H Ph 2 Me H Me H H H H 2-ClC6H4 3 Me H Me Me H H H 3-ClC6H4 4 Me H Me H H H H 4-ClC6H4 5 Me H Me H H H H 4-MeC6H4 6 Me H Me H H H H 4-t-BuC6H4 7 Me H Me H H H H 1-Naph 8 Me H Me H H H H thiophene-2-yl 9 Me H Me H H H H pyridine-3-yl 10 Me H Me Me H H H 4-ClC6H4 11 Me H Et H H H H Ph 12 Me H Et H H H H 2-ClC6H4 13 Me H Et H H H H 3-ClC6H4 14 Me H Et H H H H 4-ClC6H4 15 Me H Et H H H H 4-MeC6H4 16 Me H Et H H H H 4-t-BuC6H4 17 Me H Et H H H H 1-Naph 18 Me H Et H H H H thiophene-2-yl 19 Me H Et H H H H 2-methyl pyridine-5-yl 20 Me H Et Me H H H 4-ClC6H4 21 Me H n-Pr H H H H Ph 22 Me H n-Pr H H H H 2-ClC6H4 23 Me H n-Pr H H H H 4-ClC6H4 24 Me H n-Pr H H H H 4-MeC6H4 25 Me H n-Pr H H H H 4-EtC6H4 26 Me H i-Pr H H H H Ph 27 Me H i-Pr H H H H 4-ClC6H4 28 Me H i-Pr H H H H 3,4-Cl2C6H3 29 Me H i-Pr H H H H 2-MeC6H4 30 Me H i-Pr H H H H 4-MeC6H4 31 Me H i-Pr H H H H 4-EtC6H4 32 Me H i-Pr H H H H 2-Naph 33 Me H i-Pr H H H H 5-methyl thiophene-2-yl 34 Me H i-Pr H H H H pyridine-3-yl 35 Me H i-Pr Me H H H 4-MeC6H4 36 Me H s-Bu H H H H Ph 37 Me H s-Bu H H H H 4-ClC6H4 38 Me H s-Bu H H H H 3,4-Cl2C6H3 39 Me H s-Bu H H H H 2-MeC6H4 40 Me H s-Bu H H H H 4-MeC6H4 41 Me H s-Bu H H H H 4-t-BuC6H4 42 Me H s-Bu H H H H 1-Naph 43 Me H s-Bu H H H H thiophene-2-yl 44 Me H s-Bu H H H H isothiazole-5-yl 45 Me H s-Bu Me H H H 4-CF3C6H4 46 Me H i-Bu H H H H Ph 47 Me H i-Bu H H H H 4-ClC6H4 48 Me H i-Bu H H H H 3,4-Cl2C6H3 49 Me H i-Bu H H H H 2-MeC6H4 50 Me H i-Bu H H H H 4-MeC6H4 51 Me H i-Bu H H H H 4-t-BuC6H4 52 Me H i-Bu H H H H 2-Naph 53 Me H i-Bu H H H H thiophene-2-yl 54 Me H i-Bu H H H H 3-methyl isothiazole-5-yl 55 Me H i-Bu Me H H H 4-ClC6H4 56 Me H t-Bu H H H H Ph 57 Me H t-Bu H H H H 4-ClC6H4 58 Me H t-Bu H H H H 3,4-Cl2C6H3 59 Me H t-Bu H H H H 2-MeC6H4 60 Me H t-Bu H H H H 4-MeC6H4 61 Me H t-Bu H H H H 4-t-BuC6H4 62 Me H t-Bu H H H H 1-Naph 63 Me H t-Bu H H H H thiophene-2-yl 64 Me H t-Bu H H H H isothiazole-5-yl 65 Me H t-Bu Me H H H 4-MeC6H4 66 Me H Ph H H H H Ph 67 Me H Ph H H H H 2-ClC6H4 68 Me H Ph H H H H 4-ClC6H4 69 Me H Ph H H H H 4-MeC6H4 70 Me H Ph H H H H 4-EtC6H4 71 Me H 4-ClC6H4 H H H H Ph 72 Me H 4-ClC6H4 H H H H 4-CF3C6H4 73 Me H 4-ClC6H4 H H H H 2-MeC6H4 74 Me H 4-ClC6H4 H H H H 4-MeC6H4 75 Me H 4-ClC6H4 H H H H 4-t-BuC6H4 76 Me H Bn H H H H Ph 77 Me H Bn H H H H 4-CF3C6H4 78 Me H Bn H H H H 2-MeC6H4 79 Me H Bn H H H H 4-MeC6H4 80 Me H Bn H H H H 4-EtC6H4 81 Me H -(CH2)2- H H H 4-ClC6H4 82 Me H -(CH2)4- H H H 4-ClC6H4 83 Et H Me H H H H Ph 84 Et H Me H H H H 2-ClC6H4 85 Et H Me H Me H H 3-ClC6H4 86 Et H Me H H H H 4-ClC6H4 87 Et H Me H H H H 4-MeC6H4 88 Et H Me H H H H 4-t-BuC6H4 89 Et H Me H H H H 1-Naph 90 Et H Me H H H H 5-chloro thiophene-2-yl 91 Et H Me H H H H pyridine-3-yl 92 Et H Me Me H H H 4-ClC6H4 93 Et H Et H H H H Ph 94 Et H Et H H H H 2-ClC6H4 95 Et H Et H H H H 3-ClC6H4 96 Et H Et H H H H 4-ClC6H4 97 Et H Et H H H H 4-MeC6H4 98 Et H Et H H H H 4-t-BuC6H4 99 Et H Et H H H H 1-Naph 100 Et H Et H H H H thiophene-2-yl 101 Et H Et H H H H pyridine-3-yl 102 Et H Et Me H H H 4-ClC6H4 103 Et H i-Pr H H H H Ph 104 Et H i-Pr H H H H 4-ClC6H4 105 Et H i-Pr H H H H 3,4-Cl2C6H3 106 Et H i-Pr H H H H 2-MeC6H4 107 Et H i-Pr H H H H 4-MeC6H4 108 Et H i-Pr H H H H 4-EtC6H4 109 Et H i-Pr H H H H 2-Naph 110 Et H i-Pr H H H H thiophene-2-yl 111 Et H i-Pr H H H H 4-chloro pyridine-3-yl 112 Et H i-Pr Me H H H 4-MeC6H4 113 Et H s-Bu H H H H Ph 114 Et H s-Bu H H H H 4-ClC6H4 115 Et H s-Bu H H H H 3,4-Cl2C6H3 116 Et H s-Bu H H H H 2-MeC6H4 117 Et H s-Bu H H H H 4-MeC6H4 118 Et H s-Bu H H H H 4-t-BuC6H4 119 Et H s-Bu H H H H 1-Naph 120 Et H s-Bu H H H H thiophene-2-yl 121 Et H s-Bu H H H H isothiazole-5-yl 122 Et H s-Bu Me H H H 4-MeC6H4 123 Et H i-Bu H H H H Ph 124 Et H i-Bu H H H H 4-ClC6H4 125 Et H i-Bu H H H H 3,4-Cl2C6H3 126 Et H i-Bu H H H H 2-MeC6H4 127 Et H i-Bu H H H H 4-MeC6H4 128 Et H i-Bu H H H H 4-t-BuC6H4 129 Et H i-Bu H H H H 1-Naph 130 Et H i-Bu H H H H thiophene-2-yl 131 Et H i-Bu H H H H isothiazole-5-yl 132 Et H i-Bu Me H H H 4-MeC6H4 133 Et H i-Bu H H H H Ph 134 Et H t-Bu H H H H 4-ClC6H4 135 Et H t-Bu H H H H 3,4-Cl2C6H3 136 Et H t-Bu H H H H 2-MeC6H4 137 Et H t-Bu H H H H 4-MeC6H4 138 Et H t-Bu H H H H 4-t-BuC6H4 139 Et H t-Bu H H H H 1-Naph 140 Et H t-Bu H H H H thiophene-2-yl 141 Et H t-Bu H H H H isothiazole-5-yl 142 Et H t-Bu Me H H H 4-MeC6H4 143 Et H Ph H H H H Ph 144 Et H Ph H H H H 2-ClC6H4 145 Et H Ph H H H H 4-ClC6H4 146 Et H Ph H H H H 4-MeC6H4 147 Et H Ph H H H H 4-EtC6H4 148 n-Pr H Me H H H H Ph 149 n-Pr H Me H H H H 2-ClC6H4 150 n-Pr H Me Me H H H 3-ClC6H4 151 n-Pr H Me H H H H 4-ClC6H4 152 n-Pr H Me H H H H 4-MeC6H4 153 n-Pr H Me H H H H 4-t-BuC6H4 154 n-Pr H Me H H H H 1-Naph 155 n-Pr H Me H H H H 5-ethyl thiophene-2-yl 156 n-Pr H Me H H H H pyridine-3-yl 157 n-Pr H Me Me H H H 4-ClC6H4 158 n-Pr H Et H Et H H Ph 159 n-Pr H Et H Et H H 2-ClC6H4 160 n-Pr H Et H Et H H 3-ClC6H4 161 n-Pr H Et H Et H H 4-ClC6H4 162 n-Pr H Et H Et H H 4-MeC6H4 163 n-Pr H Et H Et H H 4-t-BuC6H4 164 n-Pr H Et H Et H H 1-Naph 165 n-Pr H Et H Et H H thiophene-2-yl 166 n-Pr H Et H Et H H pyridine-3-yl 167 n-Pr H Et Me Et H H 4-ClC6H4 168 n-Pr H i-Pr H H H H Ph 168 n-Pr H i-Pr H H H H 4-ClC6H4 169 n-Pr H i-Pr H H H H 3,4-Cl2C6H3 170 n-Pr H i-Pr H H H H 2-MeC6H4 171 n-Pr H i-Pr H H H H 4-MeC6H4 172 n-Pr H i-Pr H H H H 4-EtC6H4 173 n-Pr H i-Pr H H H H 2-Naph 174 n-Pr H i-Pr H H H H thiophene-2-yl 175 n-Pr H i-Pr H H H H 5-methyl pyridine-3-yl 176 n-Pr H i-Pr Me H H H 4-MeC6H4 177 n-Pr H s-Bu H Me Me H Ph 178 n-Pr H s-Bu H Me Me H 4-ClC6H4 179 n-Pr H s-Bu H Me Me H 3,4-Cl2C6H3 180 n-Pr H s-Bu H Me Me H 2-MeC6H4 181 n-Pr H s-Bu H Me Me H 4-MeC6H4 182 n-Pr H s-Bu H Me Me H 4-t-BuC6H4 183 n-Pr H s-Bu H Me Me H 1-Naph 184 n-Pr H s-Bu H Me Me H thiophene-2-yl 185 n-Pr H s-Bu H Me Me H isothiazole-5-yl 186 n-Pr H s-Bu Me Me Me H 4-MeC6H4 187 n-Pr H i-Bu H H H H 4-ClC6H4 188 n-Pr H i-Bu H H H H 3,4-Cl2C6H3 189 n-Pr H i-Bu H H H H 2-MeC6H4 190 n-Pr H i-Bu H H H H 4-MeC6H4 191 n-Pr H i-Bu H H H H 4-t-BuC6H4 192 n-Pr H i-Bu H H H H 1-Naph 193 n-Pr H i-Bu H H H H thiophene-2-yl 194 n-Pr H i-Bu H H H H isothiazole-5-yl 195 n-Pr H i-Bu Me H H H 4-MeC6H4 196 n-Pr H t-Bu H H H H Ph 197 n-Pr H t-Bu H H H H 4-ClC6H4 198 n-Pr H t-Bu H H H H 3,4-Cl2C6H3 199 n-Pr H t-Bu H H H H 2-MeC6H4 200 n-Pr H t-Bu H H H H 4-MeC6H4 201 n-Pr H t-Bu H H H H 4-t-BuC6H4 202 n-Pr H t-Bu H H H H 1-Naph 203 n-Pr H t-Bu H H H H thiophene-2-yl 204 n-Pr H t-Bu H H H H isothiazole-5-yl 205 n-Pr H t-Bu Me H H H 4-MeC6H4 206 n-Pr H Ph H H H H Ph 207 n-Pr H Ph H H H H 2-ClC6H4 208 n-Pr H Ph H H H H 4-ClC6H4 209 n-Pr H Ph H H H H 4-MeC6H4 210 n-Pr H Ph H H H H 4-EtC6H4 211 i-Pr H Me H H H H Ph 212 i-Pr H Me H H H H 2-ClC6H4 213 i-Pr H Me H Me H H 3-ClC6H4 214 i-Pr H Me H H H H 4-ClC6H4 215 i-Pr H Me H H H H 4-MeC6H4 216 i-Pr H Me H H H H 4-t-BuC6H4 217 i-Pr H Me H H H H 1-Naph 218 i-Pr H Me H H H H thiophene-2-yl 219 i-Pr H Me H H H H pyridine-3-yl 220 i-Pr H Me Me H H H 4-ClC6H4 221 i-Pr H Et H H H H Ph 222 i-Pr H Et H H H H 2-ClC6H4 223 i-Pr H Et H H H H 3-ClC6H4 224 i-Pr H Et H H H H 4-ClC6H4 225 i-Pr H Et H H H H 4-MeC6H4 226 i-Pr H Et H H H H 4-t-BuC6H4 227 i-Pr H Et H H H H 1-Naph 228 i-Pr H Et H H H H thiophene-2-yl 229 i-Pr H Et H H H H 2-methyl pyridine-5-yl 230 i-Pr H Et Me H H H 4-ClC6H4 231 i-Pr H n-Pr H H H H Ph 232 i-Pr H n-Pr H H H H 2-ClC6H4 233 i-Pr H n-Pr H H H H 4-ClC6H4 234 i-Pr H n-Pr H H H H 4-MeC6H4 235 i-Pr H n-Pr H H H H 4-EtC6H4 236 i-Pr H i-Pr H H H H Ph 237 i-Pr H i-Pr H H H H 4-ClC6H4 238 i-Pr H i-Pr H H H H 3,4-Cl2C6H3 239 i-Pr H i-Pr H H H H 2-MeC6H4 240 i-Pr H i-Pr H H H H 4-MeC6H4 241 i-Pr H i-Pr H H H H 4-EtC6H4 242 i-Pr H i-Pr H H H H 2-Naph 243 i-Pr H i-Pr H H H H 5-methyl thiophene-2-yl 244 i-Pr H i-Pr H H H H pyridine-3-yl 245 i-Pr H i-Pr Me H H H 4-MeC6H4 246 i-Pr H i-Pr H Me H H 4-MeC6H4 247 i-Pr H i-Pr H Me H H 4-ClC6H4 248 i-Pr H s-Bu H H H H 3,4-Cl2C6H3 249 i-Pr H s-Bu H H H H 2-MeC6H4 250 i-Pr H s-Bu H H H H 4-MeC6H4 251 i-Pr H s-Bu H H H H 4-t-BuC6H4 252 i-Pr H s-Bu H H H H 1-Naph 253 i-Pr H s-Bu H H H H thiophene-2-yl 254 i-Pr H s-Bu H H H H isothiazole-5-yl 255 i-Pr H s-Bu Me H H H 4-CF3C6H4 256 i-Pr H i-Bu H H H H Ph 257 i-Pr H i-Bu H H H H 4-ClC6H4 258 i-Pr H i-Bu H H H H 3,4-Cl2C6H3 259 i-Pr H i-Bu H H H H 2-MeC6H4 260 i-Pr H i-Bu H H H H 4-MeC6H4 261 i-Pr H i-Bu H H H H 4-t-BuC6H4 262 i-Pr H i-Bu H H H H 2-Naph 263 i-Pr H i-Bu H H H H thiophene-2-yl 264 i-Pr H i-Bu H H H H 3-methyl isothiazole- 5-yl 265 i-Pr H i-Bu Me H H H 4-ClC6H4 266 i-Pr H t-Bu H H H H Ph 267 i-Pr H t-Bu H H H H 4-ClC6H4 268 i-Pr H t-Bu H H H H 3,4-Cl2C6H3 269 i-Pr H t-Bu H H H H 2-MeC6H4 270 i-Pr H t-Bu H H H H 4-MeC6H4 271 i-Pr H t-Bu H H H H 4-t-BuC6H4 272 i-Pr H t-Bu H H H H 1-Naph 273 i-Pr H t-Bu H H H H thiophene-2-yl 274 i-Pr H t-Bu H H H H isothiazole-5-yl 275 i-Pr H t-Bu Me H H H 4-MeC6H4 276 i-Pr H Ph H H H H Ph 277 i-Pr H Ph H H H H 2-ClC6H4 278 i-Pr H Ph H H H H 4-ClC6H4 279 i-Pr H Ph H H H H 4-MeC6H4 280 i-Pr H Ph H H H H 4-EtC6H4 281 i-Pr H 4-ClC6H4 H H H H Ph 282 i-Pr H 4-ClC6H4 H H H H 4-CF3C6H4 283 i-Pr H 4-ClC6H4 H H H H 2-MeC6H4 284 i-Pr H 4-ClC6H4 H H H H 4-MeC6H4 285 i-Pr H 4-ClC6H4 H H H H 4-t-BuC6H4 286 i-Pr H Bn H H H H Ph 287 i-Pr H Bn H H H H 4-CF3C6H4 288 i-Pr H Bn H H H H 2-MeC6H4 289 i-Pr H Bn H H H H 4-MeC6H4 290 i-Pr H Bn H H H H 4-ClC6H4 291 i-Pr H -(CH2)4- H H H 4-ClC6H4 292 i-Pr H -(CH2)5- H H H 4-ClC6H4 293 s-Bu H Me H H H H Ph 294 s-Bu H Me H H H H 2-ClC6H4 295 s-Bu H Me H Me H H 3-ClC6H4 296 s-Bu H Me H H H H 4-ClC6H4 297 s-Bu H Me H H H H 4-MeC6H4 298 s-Bu H Me H H H H 4-t-BuC6H4 299 s-Bu H Me H H H H 1-Naph 300 s-Bu H Me H H H H 3-methyl thiophene-2-yl 301 s-Bu H Me H H H H pyridine-3-yl 302 s-Bu H Me Me H H H 4-ClC6H4 303 s-Bu Ac Et H H H H Ph 304 s-Bu Ac Et H H H H 2-ClC6H4 305 s-Bu Ac Et H H H H 3-ClC6H4 306 s-Bu Ac Et H H H H 4-ClC6H4 307 s-Bu Ac Et H H H H 4-MeC6H4 308 s-Bu Ac Et H H H H 4-t-BuC6H4 309 s-Bu Ac Et H H H H 1-Naph 310 s-Bu Ac Et H H H H thiophene-2-yl 311 s-Bu Ac Et H H H H pyridine-3-yl 312 s-Bu Ac Et Me H H H 4-ClC6H4 313 s-Bu H i-Pr H H H H Ph 314 s-Bu H i-Pr H H H H 4-ClC6H4 315 s-Bu H i-Pr H H H H 3,4-Cl2C6H3 316 s-Bu H i-Pr H H H H 2-MeC6H4 317 s-Bu H i-Pr H H H H 4-MeC6H4 318 s-Bu H i-Pr H H H H 4-EtC6H4 319 s-Bu H i-Pr H H H H 2-Naph 320 s-Bu H i-Pr H H H H thiophene-2-yl 321 s-Bu H i-Pr H H H H 5-methyl pyridine-3-yl 322 s-Bu H i-Pr Me H H H 4-MeC6H4 323 s-Bu H s-Bu H H H Bz Ph 324 s-Bu H s-Bu H H H Bz 4-ClC6H4 325 s-Bu H s-Bu H H H Bz 3,4-Cl2C6H3 326 s-Bu H s-Bu H H H Bz 2-MeC6H4 327 s-Bu H s-Bu H H H Bz 4-MeC6H4 328 s-Bu H s-Bu H H H Bz 4-t-BuC6H4 329 s-Bu H s-Bu H H H Bz 1-Naph 330 s-Bu H s-Bu H H H Bz thiophene-2-yl 331 s-Bu H s-Bu H H H Bz isothiazole-5-yl 332 s-Bu H s-Bu Me H H Bz 4-MeC6H4 333 s-Bu H i-Bu H H H H Ph 334 s-Bu H i-Bu H H H H 4-ClC6H4 335 s-Bu H i-Bu H H H H 3,4-Cl2C6H3 336 s-Bu H i-Bu H H H H 2-MeC6H4 337 s-Bu H i-Bu H H H H 4-MeC6H4 338 s-Bu H i-Bu H H H H 4-t-BuC6H4 339 s-Bu H i-Bu H H H H 1-Naph 340 s-Bu H i-Bu H H H H thiophene-2-yl 341 s-Bu H i-Bu H H H H isothiazole-5-yl 342 s-Bu H i-Bu Me H H H 4-MeC6H4 343 s-Bu H t-Bu H H H H Ph 344 s-Bu H t-Bu H H H H 4-ClC6H4 345 s-Bu H t-Bu H H H H 3,4-Cl2C6H3 346 s-Bu H t-Bu H H H H 2-MeC6H4 347 s-Bu H t-Bu H H H H 4-MeC6H4 348 s-Bu H t-Bu H H H H 4-t-BuC6H4 349 s-Bu H t-Bu H H H H 1-Naph 350 s-Bu H t-Bu H H H H thiophene-2-yl 351 s-Bu H t-Bu H H H H isothiazole-5-yl 352 s-Bu H t-Bu Me H H H 4-MeC6H4 353 s-Bu H Ph H H H H Ph 354 s-Bu H Ph H H H H 2-ClC6H4 355 s-Bu H Ph H H H H 4-ClC6H4 356 s-Bu H Ph H H H H 4-MeC6H4 357 s-Bu H Ph H H H H 4-EtC6H4 358 i-Bu H Me H H H H Ph 359 i-Bu H Me H H H H 2-ClC6H4 360 i-Bu H Me Me H H H 3-ClC6H4 361 i-Bu H Me H H H H 4-ClC6H4 362 i-Bu H Me H H H H 4-MeC6H4 363 i-Bu H Me H H H H 4-t-BuC6H4 364 i-Bu H Me H H H H 1-Naph 365 i-Bu H Me H H H H thiophene-2-yl 366 i-Bu H Me H H H H pyridine-3-yl 367 i-Bu H Me Me H H H 4-ClC6H4 368 i-Bu H Et H H H H Ph 369 i-Bu H Et H H H H 2-ClC6H4 370 i-Bu H Et H H H H 3-ClC6H4 371 i-Bu H Et H H H H 4-ClC6H4 372 i-Bu H Et H H H H 4-MeC6H4 373 i-Bu H Et H H H H 4-t-BuC6H4 374 i-Bu H Et H H H H 1-Naph 375 i-Bu H Et H H H H thiophene-2-yl 376 i-Bu H Et H H H H 2-methyl pyridine- 5-yl 377 i-Bu H Et Me H H H 4-ClC6H4 378 i-Bu H n-Pr H H H H Ph 379 i-Bu H n-Pr H H H H 2-ClC6H4 380 i-Bu H n-Pr H H H H 4-ClC6H4 381 i-Bu H n-Pr H H H H 4-MeC6H4 382 i-Bu H n-Pr H H H H 4-EtC6H4 383 i-Bu H i-Pr H H H H Ph 384 i-Bu H i-Pr H H H H 4-ClC6H4 385 i-Bu H i-Pr H H H H 3,4-Cl2C6H3 386 i-Bu H i-Pr H H H H 2-MeC6H4 387 i-Bu H i-Pr H H H H 4-MeC6H4 388 i-Bu H i-Pr H H H H 4-EtC6H4 389 i-Bu H i-Pr H H H H 2-Naph 390 i-Bu H i-Pr H H H H 5-methyl thiophene- 2-yl 391 i-Bu H i-Pr H H H H pyridine-3-yl 392 i-Bu H i-Pr Me H H H 4-MeC6H4 393 i-Bu H s-Bu H H H H Ph 394 i-Bu H s-Bu H H H H 4-ClC6H4 395 i-Bu H s-Bu H H H H 3,4-Cl2C6H3 396 i-Bu H s-Bu H H H H 2-MeC6H4 397 i-Bu H s-Bu H H H H 4-MeC6H4 398 i-Bu H s-Bu H H H H 4-t-BuC6H4 399 i-Bu H s-Bu H H H H 1-Naph 400 i-Bu H s-Bu H H H H thiophene-2-yl 401 i-Bu H s-Bu H H H H isothiazole-5-yl 402 i-Bu H s-Bu Me H H H 4-CF3C6H4 403 i-Bu H i-Bu H H H H Ph 404 i-Bu H i-Bu H H H H 4-ClC6H4 405 i-Bu H i-Bu H H H H 3,4-Cl2C6H3 406 i-Bu H i-Bu H H H H 2-MeC6H4 407 i-Bu H i-Bu H H H H 4-MeC6H4 408 i-Bu H i-Bu H H H H 4-t-BuC6H4 409 i-Bu H i-Bu H H H H 2-Naph 410 i-Bu H i-Bu H H H H thiophene-2-yl 411 i-Bu H i-Bu H H H H 3-methyl isothiazole-5-yl 412 i-Bu H i-Bu Me H H H 4-ClC6H4 413 i-Bu H t-Bu H H H H Ph 414 i-Bu H t-Bu H H H H 4-ClC6H4 415 i-Bu H t-Bu H H H H 3,4-Cl2C6H3 416 i-Bu H t-Bu H H H H 2-MeC6H4 417 i-Bu H t-Bu H H H H 4-MeC6H4 418 i-Bu H t-Bu H H H H 4-t-BuC6H4 419 i-Bu H t-Bu H H H H 1-Naph 420 i-Bu H t-Bu H H H H thiophene-2-yl 421 i-Bu H t-Bu H H H H isothiazole-5-yl 422 i-Bu H t-Bu Me H H H 4-MeC6H4 423 i-Bu H Ph H H H H Ph 424 i-Bu H Ph H H H H 2-ClC6H4 425 i-Bu H Ph H H H H 4-ClC6H4 426 i-Bu H Ph H H H H 4-MeC6H4 427 i-Bu H Ph H H H H 4-EtC6H4 428 i-Bu H 4-ClC6H4 H H H H Ph 429 i-Bu H 4-ClC6H4 H H H H 4-CF3C6H4 430 i-Bu H 4-ClC6H4 H H H H 2-MeC6H4 431 i-Bu H 4-ClC6H4 H H H H 4-MeC6H4 432 i-Bu H 4-ClC6H4 H H H H 4-t-BuC6H4 433 i-Bu H Bn H H H H Ph 434 i-Bu H Bn H H H H 4-CF3C6H4 435 i-Bu H Bn H H H H 2-MeC6H4 436 i-Bu H Bn H H H H 4-MeC6H4 437 i-Bu H Bn H H H H 4-EtC6H4 438 i-Bu H -(CH2)4- H H H 4-ClC6H4 439 i-Bu H -(CH2)5- H H H 4-ClC6H4 440 t-Bu H Me H H H H Ph 441 t-Bu H Me H H H H 2-ClC6H4 442 t-Bu H Me H Et H H 3-ClC6H4 443 t-Bu H Me H H H H 4-ClC6H4 444 t-Bu H Me H H H H 4-MeC6H4 445 t-Bu H Me H H H H 4-t-BuC6H4 446 t-Bu H Me H H H H 1-Naph 447 t-Bu H Me H H H H 5-methyl thiophene-2-yl 448 t-Bu H Me H H H H pyridine-3-yl 449 t-Bu H Me Me H H H 4-ClC6H4 450 t-Bu Me Et H H H H Ph 451 t-Bu Me Et H H H H 2-ClC6H4 452 t-Bu Me Et H H H H 3-ClC6H4 453 t-Bu Me Et H H H H 4-ClC6H4 454 t-Bu Me Et H H H H 4-MeC6H4 455 t-Bu Me Et H H H H 4-t-BuC6H4 456 t-Bu Me Et H H H H 1-Naph 457 t-Bu Me Et H H H H thiophene-2-yl 458 t-Bu Me Et H H H H pyridine-3-yl 459 t-Bu Me Et Me H H H 4-ClC6H4 460 t-Bu H i-Pr H H H H Ph 461 t-Bu H i-Pr H H H H 4-ClC6H4 462 t-Bu H i-Pr H H H H 3,4-Cl2C6H3 463 t-Bu H i-Pr H H H H 2-MeC6H4 464 t-Bu H i-Pr H H H H 4-MeC6H4 465 t-Bu H i-Pr H H H H 4-EtC6H4 466 t-Bu H i-Pr H H H H 2-Naph 467 t-Bu H i-Pr H H H H thiophene-2-yl 468 t-Bu H i-Pr H H H H 5-methyl pyridine-3-yl 469 t-Bu H i-Pr Me H H H 4-MeC6H4 470 t-Bu H i-Pr H Me H H 4-MeC6H4 471 t-Bu H i-Pr H Me H H 4-ClC6H4 472 t-Bu H s-Bu H H H Et 3,4-Cl2C6H3 473 t-Bu H s-Bu H H H Et 2-MeC6H4 474 t-Bu H s-Bu H H H Et 4-MeC6H4 475 t-Bu H s-Bu H H H Et 4-t-BuC6H4 476 t-Bu H s-Bu H H H Et 1-Naph 478 t-Bu H s-Bu H H H Et thiophene-2-yl 479 t-Bu H s-Bu H H H Et isothiazole-5-yl 480 t-Bu H s-Bu Me H H Et 4-MeC6H4 481 t-Bu H i-Bu H H H H Ph 482 t-Bu H i-Bu H H H H 4-ClC6H4 483 t-Bu H i-Bu H H H H 3,4-Cl2C6H3 484 t-Bu H i-Bu H H H H 2-MeC6H4 485 t-Bu H i-Bu H H H H 4-MeC6H4 486 t-Bu H i-Bu H H H H 4-t-BuC6H4 487 t-Bu H i-Bu H H H H 1-Naph 488 t-Bu H i-Bu H H H H thiophene-2-yl 489 t-Bu H i-Bu H H H H isothiazole-5-yl 490 t-Bu H i-Bu Me H H H 4-MeC6H4 491 t-Bu H t-Bu H H H H Ph 492 t-Bu H t-Bu H H H H 4-ClC6H4 493 t-Bu H t-Bu H H H H 3,4-Cl2C6H3 494 t-Bu H t-Bu H H H H 2-MeC6H4 495 t-Bu H t-Bu H H H H 4-MeC6H4 496 t-Bu H t-Bu H H H H 4-t-BuC6H4 497 t-Bu H t-Bu H H H H 1-Naph 498 t-Bu H t-Bu H H H H thiophene-2-yl 499 t-Bu H t-Bu H H H H isothiazole-5-yl 500 t-Bu H t-Bu Me H H H 4-MeC6H4 501 t-Bu H Ph H H H H Ph 502 t-Bu H Ph H H H H 2-ClC6H4 503 t-Bu H Ph H H H H 4-ClC6H4 504 t-Bu H Ph H H H H 4-MeC6H4 505 t-Bu H Ph H H H H 4-EtC6H4 506 Ph H Me H H H H Ph 507 Ph H Me H H H H 2-ClC6H4 508 Ph H Me Me H H H 3-ClC6H4 509 Ph H Me H H H H 4-ClC6H4 510 Ph H Me H H H H 4-MeC6H4 511 Ph H Me H H H H 4-t-BuC6H4 512 Ph H Me H H H H 1-Naph 513 Ph H Me H H H H 5-methyl thiophene-2-yl 514 Ph H Me H H H H pyridine-3-yl 515 Ph H Me Me H H H 4-ClC6H4 516 Ph H Et H H H H Ph 517 Ph H Et H H H H 2-ClC6H4 518 Ph H Et H H H H 3-ClC6H4 519 Ph H Et H H H H 4-ClC6H4 520 Ph H Et H H H H 4-MeC6H4 521 Ph H Et H H H H 4-t-BuC6H4 522 Ph H Et H H H H 1-Naph 523 Ph H Et H H H H thiophene-2-yl 524 Ph H Et H H H H pyridine-3-yl 525 Ph H Et Me H H H 4-ClC6H4 526 Ph H i-Pr H H H H Ph 527 Ph H i-Pr H H H H 4-ClC6H4 528 Ph H i-Pr H H H H 3,4-Cl2C6H3 529 Ph H i-Pr H H H H 2-MeC6H4 530 Ph H i-Pr H H H H 4-MeC6H4 531 Ph H i-Pr H H H H 4-EtC6H4 532 Ph H i-Pr H H H H 2-Naph 533 Ph H i-Pr H H H H thiophene-2-yl 534 Ph H i-Pr H H H H 5-methyl pyridine-3-yl 535 Ph H i-Pr Me H H H 4-MeC6H4 536 Ph H allyl H H H H Ph 537 Ph H allyl H H H H 4-ClC6H4 538 Ph H allyl H H H H 3,4-Cl2C6H3 539 Ph H allyl H H H H 2-MeC6H4 540 Ph H allyl H H H H 4-MeC6H4 541 Ph H allyl H H H H 4-t-BuC6H4 542 Ph H allyl H H H H 1-Naph 543 Ph H allyl H H H H thiophene-2-yl 544 Ph H allyl H H H H isothiazole-5-yl 545 Ph H allyl Me H H H 4-MeC6H4 546 Ph H i-Bu H H H H Ph 547 Ph H i-Bu H H H H 4-ClC6H4 548 Ph H i-Bu H H H H 3,4-Cl2C6H3 549 Ph H i-Bu H H H H 2-MeC6H4 550 Ph H i-Bu H H H H 4-MeC6H4 551 Ph H i-Bu H H H H 4-t-BuC6H4 552 Ph H i-Bu H H H H 1-Naph 553 Ph H i-Bu H H H H thiophene-2-yl 554 Ph H i-Bu H H H H isothiazole-5-yl 555 Ph H i-Bu Me H H H 4-MeC6H4 556 Ph H propargyl H H H H Ph 557 Ph H propargyl H H H H 4-ClC6H4 558 Ph H propargyl H H H H 3,4-Cl2C6H3 559 Ph H propargyl H H H H 2-MeC6H4 560 Ph H propargyl H H H H 4-MeC6H4 561 Ph H propargyl H H H H 4-t-BuC6H4 562 Ph H propargyl H H H H 1-Naph 563 Ph H propargyl H H H H thiophene-2-yl 564 Ph H propargyl H H H H isothiazole-5-yl 565 Ph H propargyl Me H H H 4-MeC6H4 566 Ph H Ph H H H H Ph 567 Ph H Ph H H H H 2-ClC6H4 568 Ph H Ph H H H H 4-ClC6H4 569 Ph H Ph H H H H 4-MeC6H4 570 Ph H Ph H H H H 4-EtC6H4 571 Bn H Me H H H H Ph 572 Bn H Me H H H H 2-ClC6H4 573 Bn H Me H Me H H 3-ClC6H4 574 Bn H Me H H H H 4-ClC6H4 575 Bn H Me H H H H 4-MeC6H4 576 Bn H Me H H H H 4-t-BuC6H4 577 Bn H Me H H H H 1-Naph 578 Bn H Me H H H H thiophene-2-yl 579 Bn H Me H H H H pyridine-3-yl 580 Bn H Me Me H H H 4-ClC6H4 581 Bn H Et H H H H Ph 582 Bn H Et H H H H 2-ClC6H4 583 Bn H Et H H H H 3-ClC6H4 584 Bn H Et H H H H 4-ClC6H4 585 Bn H Et H H H H 4-MeC6H4 586 Bn H Et H H H H 4-t-BuC6H4 587 Bn H Et H H H H 1-Naph 588 Bn H Et H H H H thiophene-2-yl 589 Bn H Et H H H H 4-methyl pyridine-5-yl 590 Bn H Et Me H H H 4-ClC6H4 591 Bn H n-Pr H H H H Ph 592 Bn H n-Pr H H H H 2-ClC6H4 593 Bn H n-Pr H H H H 4-ClC6H4 594 Bn H n-Pr H H H H 4-MeC6H4 595 Bn H n-Pr H H H H 4-EtC6H4 596 Bn H i-Pr H H H H Ph 597 Bn H i-Pr H H H H 4-ClC6H4 598 Bn H i-Pr H H H H 3,4-Cl2C6H3 599 Bn H i-Pr H H H H 2-MeC6H4 600 Bn H i-Pr H H H H 4-MeC6H4 601 Bn H i-Pr H H H H 4-EtC6H4 602 Bn H i-Pr H H H H 2-Naph 603 Bn H i-Pr H H H H 5-methyl thiophene-2-yl 604 Bn H i-Pr H H H H pyridine-3-yl 605 Bn H i-Pr Me H H H 4-MeC6H4 606 Bn H s-Bu H H H H Ph 607 Bn H s-Bu H H H H 4-ClC6H4 608 Bn H s-Bu H H H H 3,4-Cl2C6H3 609 Bn H s-Bu H H H H 2-MeC6H4 610 Bn H s-Bu H H H H 4-MeC6H4 611 Bn H s-Bu H H H H 4-t-BuC6H4 612 Bn H s-Bu H H H H 1-Naph 613 Bn H s-Bu H H H H thiophene-2-yl 614 Bn H s-Bu H H H H isothiazole-5-yl 615 Bn H s-Bu Me H H H 4-CF3C6H4 616 Bn H i-Bu H H H H Ph 617 Bn H i-Bu H H H H 4-ClC6H4 618 Bn H i-Bu H H H H 3,4-Cl2C6H3 619 Bn H i-Bu H H H H 2-MeC6H4 620 Bn H i-Bu H H H H 4-MeC6H4 621 Bn H i-Bu H H H H 4-t-BuC6H4 622 Bn H i-Bu H H H H 2-Naph 623 Bn H i-Bu H H H H thiophene-2-yl 624 Bn H i-Bu H H H H 3-methyl isothiazole-5-yl 625 Bn H i-Bu Me H H H 4-ClC6H4 626 Bn H t-Bu H H H H Ph 627 Bn H t-Bu H H H H 4-ClC6H4 628 Bn H t-Bu H H H H 3,4-Cl2C6H3 629 Bn H t-Bu H H H H 2-MeC6H4 630 Bn H t-Bu H H H H 4-MeC6H4 631 Bn H t-Bu H H H H 4-t-BuC6H4 632 Bn H t-Bu H H H H 1-Naph 633 Bn H t-Bu H H H H thiophene-2-yl 634 Bn H t-Bu H H H H isothiazole-5-yl 635 Bn H t-Bu Me H H H 4-MeC6H4 636 Bn H Ph H H H H Ph 637 Bn H Ph H H H H 2-ClC6H4 638 Bn H Ph H H H H 4-ClC6H4 639 Bn H Ph H H H H 4-MeC6H4 640 Bn H Ph H H H H 4-EtC6H4 641 Bn H 4-MeC6H4 H H H H Ph 642 Bn H 4-MeC6H4 H H H H 4-CF3C6H4 643 Bn H 4-MeC6H4 H H H H 2-MeC6H4 644 Bn H 4-MeC6H4 H H H H 4-MeC6H4 645 Bn H 4-MeC6H4 H H H H 4-t-BuC6H4 646 Bn H Bn H H H H Ph 647 Bn H Bn H H H H 4-CF3C6H4 648 Bn H Bn H H H H 2-MeC6H4 649 Bn H Bn H H H H 4-MeC6H4 650 Bn H Bn H H H H 4-EtC6H4 651 Bn H -(CH2)4- H H H 4-ClC6H4 652 Bn H -(CH2)5- H H H 4-ClC6H4 653 2-Naph H Me H H H H Ph 654 2-Naph H Me H H H H 2-BrC6H4 655 2-Naph H Me Me H H H 3-BrC6H4 656 2-Naph H Me H H H H 4-BrC6H4 657 2-Naph H Me H H H H 4-MeC6H4 658 2-Naph H Me H H H H 4-t-BuC6H4 659 2-Naph H Me H H H H 1-Naph 660 2-Naph H Me H H H H 5-methyl thiophene-2-yl 661 2-Naph H Me H H H H pyridine-3-yl 662 2-Naph H Me Me H H H 4-ClC6H4 663 2-Naph H Et H H H H Ph 664 2-Naph H Et H H H H 2-FC6H4 665 2-Naph H Et H H H H 3-FC6H4 666 2-Naph H Et H H H H 4-FC6H4 667 2-Naph H Et H H H H 4-MeC6H4 668 2-Naph H Et H H H H 4-t-BuC6H4 669 2-Naph H Et H H H H 1-Naph 670 2-Naph H Et H H H H thiophene-2-yl 671 2-Naph H Et H H H H pyridine-3-yl 672 2-Naph H Et Me H H H 4-ClC6H4 673 2-Naph H i-Pr H H H H Ph 674 2-Naph H i-Pr H H H H 4-ClC6H4 675 2-Naph H i-Pr H H H H 3,4-Cl2C6H3 676 2-Naph H i-Pr H H H H 2-MeC6H4 677 2-Naph H i-Pr H H H H 4-MeC6H4 678 2-Naph H i-Pr H H H H 4-EtC6H4 679 2-Naph H i-Pr H H H H 2-Naph 680 2-Naph H i-Pr H H H H thiophene-2-yl 681 2-Naph H i-Pr H H H H 5-methyl pyridine- 3-yl 682 2-Naph H i-Pr Me H H H 4-MeC6H4 683 2-Naph H s-Bu H H H H Ph 684 2-Naph H s-Bu H H H H 4-ClC6H4 685 2-Naph H s-Bu H H H H 3,4-Cl2C6H3 686 2-Naph H s-Bu H H H H 2-MeC6H4 687 2-Naph H s-Bu H H H H 4-MeC6H4 688 2-Naph H s-Bu H H H H 4-t-BuC6H4 689 2-Naph H s-Bu H H H H 1-Naph 690 2-Naph H s-Bu H H H H thiophene-2-yl 691 2-Naph H s-Bu H H H H isothiazole-5-yl 692 2-Naph H s-Bu Me H H H 4-MeC6H4 693 2-Naph H i-Bu H H H H Ph 694 2-Naph H i-Bu H H H H 4-ClC6H4 695 2-Naph H i-Bu H H H H 3,4-Cl2C6H3 696 2-Naph H i-Bu H H H H 2-MeC6H4 697 2-Naph H i-Bu H H H H 4-MeC6H4 698 2-Naph H i-Bu H H H H 4-t-BuC6H4 699 2-Naph H i-Bu H H H H 1-Naph 700 2-Naph H i-Bu H H H H thiophene-2-yl 701 2-Naph H i-Bu H H H H isothiazole-5-yl 702 2-Naph H i-Bu Me H H H 4-MeC6H4 703 2-Naph H c-Hex H H H H Ph 704 2-Naph H c-Hex H H H H 4-ClC6H4 705 2-Naph H c-Hex H H H H 3,4-Cl2C6H3 706 2-Naph H c-Hex H H H H 2-MeC6H4 707 2-Naph H c-Hex H H H H 4-MeC6H4 708 2-Naph H c-Hex H H H H 4-t-BuC6H4 709 2-Naph H c-Hex H H H H 1-Naph 710 2-Naph H c-Hex H H H H thiophene-2-yl 711 2-Naph H c-Hex H H H H isothiazole-5-yl 712 2-Naph H c-Hex Me H H H 4-MeC6H4 713 2-Naph H Ph H H H H Ph 714 2-Naph H Ph H H H H 2-ClC6H4 715 2-Naph H Ph H H H H 4-ClC6H4 716 2-Naph H Ph H H H H 4-MeC6H4 717 2-Naph H Ph H H H H 4-EtC6H4 718 allyl H Me H H H H Ph 719 allyl H Me H H H H 2-ClC6H4 720 allyl H Me Me H H H 3-ClC6H4 721 allyl H Me H H H H 4-ClC6H4 722 allyl H Me H H H H 4-CNC6H4 723 allyl H Me H H H H 4-t-BuC6H4 724 allyl H Me H H H H 1-Naph 725 allyl H Me H H H H 5-methyl thiophene-2-yl 726 allyl H Me H H H H pyridine-3-yl 727 allyl H Me Me H H H 4-CF3C6H4 728 allyl H Et H H H H Ph 729 allyl H Et H H H H 2-ClC6H4 730 allyl H Et H H H H 3-ClC6H4 731 allyl H Et H H H H 4-ClC6H4 732 allyl H Et H H H H 4-MeC6H4 733 allyl H Et H H H H 4-t-BuC6H4 734 allyl H Et H H H H 1-Naph 735 allyl H Et H H H H thiophene-2-yl 736 allyl H Et H H H H pyridine-3-yl 737 allyl H Et Me H H H 4-ClC6H4 738 allyl H i-Pr H H H H Ph 739 allyl H i-Pr H H H H 4-ClC6H4 740 allyl H i-Pr H H H H 3,4-Cl2C6H3 741 allyl H i-Pr H H H H 2-MeC6H4 742 allyl H i-Pr H H H H 4-MeC6H4 743 allyl H i-Pr H H H H 4-EtC6H4 744 allyl H i-Pr H H H H 2-Naph 745 allyl H i-Pr H H H H thiophene-2-yl 746 allyl H i-Pr H H H H 5-methyl pyridine-3-yl 747 allyl H i-Pr Me H H H 4-MeC6H4 748 allyl H s-Bu H H H H Ph 749 allyl H s-Bu H H H H 4-ClC6H4 750 allyl H s-Bu H H H H 3,4-Cl2C6H3 751 allyl H s-Bu H H H H 2-MeC6H4 752 allyl H s-Bu H H H H 4-MeC6H4 753 allyl H s-Bu H H H H 4-t-BuC6H4 754 allyl H s-Bu H H H H 1-Naph 755 allyl H s-Bu H H H H thiophene-2-yl 756 allyl H s-Bu H H H H isothiazole-5-yl 757 allyl H s-Bu Me H H H 4-MeC6H4 758 allyl H i-Bu H H H H Ph 759 allyl H i-Bu H H H H 4-ClC6H4 760 allyl H i-Bu H H H H 3,4-Cl2C6H3 761 allyl H i-Bu H H H H 2-MeC6H4 762 allyl H i-Bu H H H H 4-MeC6H4 763 allyl H i-Bu H H H H 4-t-BuC6H4 764 allyl H i-Bu H H H H 1-Naph 765 allyl H i-Bu H H H H thiophene-2-yl 766 allyl H i-Bu H H H H isothiazole-5-yl 767 allyl H i-Bu Me H H H 4-MeC6H4 768 allyl H t-Bu H H H H Ph 769 allyl H t-Bu H H H H 4-ClC6H4 770 allyl H t-Bu H H H H 3,4-Cl2C6H3 771 allyl H t-Bu H H H H 2-MeC6H4 772 allyl H t-Bu H H H H 4-MeC6H4 773 allyl H t-Bu H H H H 4-t-BuC6H4 774 allyl H t-Bu H H H H 1-Naph 775 allyl H t-Bu H H H H thiophene-2-yl 776 allyl H t-Bu H H H H isothiazole-5-yl 777 allyl H t-Bu Me H H H 4-MeC6H4 778 allyl H Ph H H H H Ph 779 allyl H Ph H H H H 2-ClC6H4 780 allyl H 4-FC6H4 H H H H 4-ClC6H4 781 allyl H Ph H H H H 4-MeC6H4 782 allyl H 4-BrC6H4 H H H H 4-EtC6H4 783 propargyl H Me H H H H Ph 784 propargyl H Me H H H H 2-IC6H4 785 propargyl H Me H Me Me H 3-IC6H4 786 propargyl H Me H H H H 4-IC6H4 787 propargyl H Me H H H H 4-MeC6H4 788 propargyl H Me H H H H 4-t-BuC6H4 789 propargyl H Me H H H H 1-Naph 790 propargyl H Me H H H H 5-methyl thiophene-2-yl 791 propargyl H Me H H H H pyridine-3-yl 792 propargyl H Me Me H H H 4-ClC6H4 793 propargyl H Et H H H H Ph 794 propargyl H Et H H H H 2-ClC6H4 795 propargyl H Et H H H H 3-ClC6H4 796 propargyl H Et H H H H 4-ClC6H4 797 propargyl H Et H H H H 4-MeC6H4 798 propargyl H Et H H H H 4-t-BuC6H4 799 propargyl H Et H H H H 1-Naph 800 propargyl H Et H H H H thiophene-2-yl 801 propargyl H Et H H H H pyridine-3-yl 802 propargyl H Et Me H H H 4-ClC6H4 803 propargyl H i-Pr H H H H Ph 804 propargyl H i-Pr H H H H 4-ClC6H4 805 propargyl H i-Pr H H H H 3,4-Cl2C6H3 806 propargyl H i-Pr H H H H 2-MeC6H4 807 propargyl H i-Pr H H H H 4-MeC6H4 808 propargyl H i-Pr H H H H 4-EtC6H4 809 propargyl H i-Pr H H H H 2-Naph 810 propargyl H i-Pr H H H H thiophene-2-yl 811 propargyl H i-Pr H H H H 5-methyl pyridine-3-yl 812 propargyl H i-Pr Me H H H 4-MeC6H4 813 propargyl H s-Bu H H H H Ph 814 propargyl H s-Bu H H H H 4-ClC6H4 815 propargyl H s-Bu H H H H 3,4-Cl2C6H3 816 propargyl H s-Bu H H H H 2-MeC6H4 817 propargyl H s-Bu H H H H 4-MeC6H4 818 propargyl H s-Bu H H H H 4-t-BuC6H4 819 propargyl H s-Bu H H H H 1-Naph 820 propargyl H s-Bu H H H H thiophene-2-yl 821 propargyl H s-Bu H H H H isothiazole-5-yl 822 propargyl H s-Bu Me H H H 4-MeC6H4 823 propargyl H i-Bu H H H H Ph 824 propargyl H i-Bu H H H H 4-ClC6H4 825 propargyl H i-Bu H H H H 3,4-Cl2C6H3 826 propargyl H i-Bu H H H H 2-MeC6H4 827 propargyl H i-Bu H H H H 4-MeC6H4 828 propargyl H i-Bu H H H H 4-t-BuC6H4 829 propargyl H i-Bu H H H H 1-Naph 830 propargyl H i-Bu H H H H thiophene-2-yl 831 propargyl H i-Bu H H H H isothiazole-5-yl 832 propargyl H i-Bu Me H H H 4-MeC6H4 833 propargyl H t-Bu H H H H Ph 834 propargyl H t-Bu H H H H 4-ClC6H4 835 propargyl H t-Bu H H H H 3,4-Cl2C6H3 836 propargyl H t-Bu H H H H 2-MeC6H4 837 propargyl H t-Bu H H H H 4-MeC6H4 838 propargyl H t-Bu H H H H 4-t-BuC6H4 839 propargyl H t-Bu H H H H 1-Naph 840 propargyl H t-Bu H H H H thiophene-2-yl 841 propargyl H t-Bu H H H H isothiazole-5-yl 842 propargyl H t-Bu Me H H H 4-MeC6H4 843 propargyl H Ph H Bn H H Ph 844 propargyl H Ph H H H H 2-ClC6H4 845 propargyl H 4-ClC6H4 H H H H 4-ClC6H4 846 propargyl H Ph H H H H 4-MeC6H4 847 propargyl H 4-MeC6H4 H H H H 4-EtC6H4 848 c-Pr H Me H H H H Ph 849 c-Pr H Me H H H H 2-ClC6H4 850 c-Pr H Me Me H H H 3-ClC6H4 851 c-Pr H Me H H H H 4-ClC6H4 852 c-Pr H Me H H H H 4-MeC6H4 853 c-Pr H Me H H H H 4-t-BuC6H4 854 c-Pr H Me H H H H 1-Naph 855 c-Pr H Me H H H H 5-methyl thiophene-2-yl 856 c-Pr H Me H H H H pyridine-3-yl 857 c-Pr H Me Me H H H 4-ClC6H4 858 c-Pr H Et H H H H Ph 859 c-Pr H Et H H H H 2-ClC6H4 860 c-Pr H Et H H H H 3-ClC6H4 861 c-Pr H Et H H H H 4-ClC6H4 862 c-Pr H Et H H H H 4-MeC6H4 863 c-Pr H Et H H H H 4-t-BuC6H4 864 c-Pr H Et H H H H 1-Naph 865 c-Pr H Et H H H H thiophene-2-yl 866 c-Pr H Et H H H H pyridine-3-yl 867 c-Pr H Et Me H H H 4-ClC6H4 868 c-Pr H i-Pr H H H H Ph 869 c-Pr H i-Pr H H H H 4-ClC6H4 870 c-Pr H i-Pr H H H H 3,4-Cl2C6H3 871 c-Pr H i-Pr H H H H 2-MeC6H4 872 c-Pr H i-Pr H H H H 4-MeC6H4 873 c-Pr H i-Pr H H H H 4-EtC6H4 874 c-Pr H i-Pr H H H H 2-Naph 875 c-Pr H i-Pr H H H H thiophene-2-yl 876 c-Pr H i-Pr H H H H 5-methyl pyridine-3-yl 878 c-Pr H i-Pr Me H H H 4-MeC6H4 879 c-Pr H s-Bu H H H H Ph 880 c-Pr H s-Bu H H H H 4-ClC6H4 881 c-Pr H s-Bu H H H H 3,4-Cl2C6H3 882 c-Pr H s-Bu H H H H 2-MeC6H4 883 c-Pr H s-Bu H H H H 4-MeC6H4 884 c-Pr H s-Bu H H H H 4-t-BuC6H4 885 c-Pr H s-Bu H H H H 1-Naph 886 c-Pr H s-Bu H H H H thiophene-2-yl 887 c-Pr H s-Bu H H H H isothiazole-5-yl 888 c-Pr H s-Bu Me H H H 4-MeC6H4 889 c-Pr H i-Bu H H H H Ph 890 c-Pr H i-Bu H H H H 4-ClC6H4 891 c-Pr H i-Bu H H H H 3,4-Cl2C6H3 892 c-Pr H i-Bu H H H H 2-MeC6H4 893 c-Pr H i-Bu H H H H 4-MeC6H4 894 c-Pr H i-Bu H H H H 4-t-BuC6H4 895 c-Pr H i-Bu H H H H 1-Naph 896 c-Pr H i-Bu H H H H thiophene-2-yl 897 c-Pr H i-Bu H H H H isothiazole-5-yl 898 c-Pr H i-Bu Me H H H 4-MeC6H4 899 c-Pr H t-Bu H Bn H H Ph 900 c-Pr H t-Bu H H H H 4-ClC6H4 901 c-Pr H t-Bu H H H H 3,4-Cl2C6H3 902 c-Pr H t-Bu H H H H 2-MeC6H4 903 c-Pr H t-Bu H H H H 4-MeC6H4 904 c-Pr H t-Bu H H H H 4-t-BuC6H4 905 c-Pr H t-Bu H H H H 1-Naph 906 c-Pr H t-Bu H H H H thiophene-2-yl 907 c-Pr H t-Bu H H H H isothiazole-5-yl 908 c-Pr H t-Bu Me H H H 4-MeC6H4 909 c-Pr H Ph H H H H Ph 910 c-Pr H Ph H H H H 2-ClC6H4 911 c-Pr H Ph H H H H 4-ClC6H4 912 c-Pr H Ph H H H H 4-MeC6H4 913 c-Pr H Ph H H H H 4-EtC6H4 914 c-Hex H Me H H H H Ph 915 c-Hex H Me H H H H 2-ClC6H4 916 c-Hex H Me H Et H H 3-ClC6H4 917 c-Hex H Me H H H H 4-ClC6H4 918 c-Hex H Me H H H H 4-MeC6H4 919 c-Hex H Me H H H H 4-t-BuC6H4 920 c-Hex H Me H H H H 1-Naph 921 c-Hex H Me H H H H 5-methyl thiophene-2-yl 922 c-Hex H Me H H H H pyridine-3-yl 923 c-Hex H Me Me H H H 4-ClC6H4 924 c-Hex H Et H H H H Ph 925 c-Hex H Et H H H H 2-ClC6H4 926 c-Hex H Et H H H H 3-ClC6H4 927 c-Hex H Et H H H H 4-ClC6H4 928 c-Hex H Et H H H H 4-MeC6H4 929 c-Hex H Et H H H H 4-t-BuC6H4 930 c-Hex H Et H H H H 1-Naph 931 c-Hex H Et H H H H thiophene-2-yl 932 c-Hex H Et H H H H pyridine-3-yl 933 c-Hex H Et Me H H H 4-ClC6H4 934 c-Hex H i-Pr H H H H Ph 935 c-Hex H i-Pr H H H H 4-ClC6H4 936 c-Hex H i-Pr H H H H 3,4-Cl2C6H3 937 c-Hex H i-Pr H H H H 2-MeC6H4 938 c-Hex H i-Pr H H H H 4-MeC6H4 939 c-Hex H i-Pr H H H H 4-EtC6H4 940 c-Hex H i-Pr H H H H 2-Naph 941 c-Hex H i-Pr H H H H thiophene-2-yl 942 c-Hex H i-Pr H H H H 5-methyl pyridine-3-yl 943 c-Hex H i-Pr Me H H H 4-MeC6H4 944 c-Hex H s-Bu H H H H Ph 945 c-Hex H s-Bu H H H H 4-ClC6H4 946 c-Hex H s-Bu H H H H 3,4-Cl2C6H3 947 c-Hex H s-Bu H H H H 2-MeC6H4 948 c-Hex H s-Bu H H H H 4-MeC6H4 949 c-Hex H s-Bu H H H H 4-t-BuC6H4 950 c-Hex H s-Bu H Ph H H 1-Naph 951 c-Hex H s-Bu H H H H thiophene-2-yl 952 c-Hex H s-Bu H H H H isothiazole-5-yl 953 c-Hex H s-Bu Me H H H 4-MeC6H4 954 c-Hex H i-Bu H H H H Ph 955 c-Hex H i-Bu H H H H 4-ClC6H4 956 c-Hex H i-Bu H H H H 3,4-Cl2C6H3 957 c-Hex H i-Bu H H H H 2-MeC6H4 958 c-Hex H i-Bu H H H H 4-MeC6H4 959 c-Hex H i-Bu H H H H 4-t-BuC6H4 960 c-Hex H i-Bu H H H H 1-Naph 961 c-Hex H i-Bu H H H H thiophene-2-yl 962 c-Hex H i-Bu H H H H isothiazole-5-yl 963 c-Hex H i-Bu Me H H H 4-MeC6H4 964 c-Hex H t-Bu H H H H Ph 965 c-Hex H t-Bu H H H H 4-ClC6H4 966 c-Hex H t-Bu H H H H 3,4-Cl2C6H3 967 c-Hex H t-Bu H H H H 2-MeC6H4 968 c-Hex H t-Bu H H H H 4-MeC6H4 969 c-Hex H t-Bu H H H H 4-t-BuC6H4 970 c-Hex H t-Bu H H H H 1-Naph 971 c-Hex H t-Bu H H H H thiophene-2-yl 972 c-Hex H t-Bu H H H H isothiazole-5-yl 973 c-Hex H t-Bu Me H H H 4-MeC6H4 974 c-Hex H Ph H H H H Ph 975 c-Hex H Ph H H H H 2-ClC6H4 976 c-Hex H Ph H H H H 4-ClC6H4 977 c-Hex H Ph H H H H 4-MeC6H4 978 c-Hex H Ph H H H H 4-EtC6H4 979 vinyl H Me H H H H Ph 980 vinyl H Me H H H H 2-ClC6H4 981 vinyl H Me Me H H H 3-ClC6H4 982 vinyl H Me H H H H 4-ClC6H4 983 vinyl H Me H H H H 4-MeC6H4 984 vinyl H Me H H H H 4-t-BuC6H4 985 vinyl H Me H H H H 1-Naph 986 vinyl H Me H H H H 5-ethyl thiophene-2-yl 987 vinyl H Me H H H H pyridine-3-yl 988 vinyl H Me Me H H H 4-ClC6H4 989 vinyl H Et H H H H Ph 990 vinyl H Et H H H H 2-ClC6H4 991 vinyl H Et H H H H 3-ClC6H4 992 vinyl H Et H H H H 4-ClC6H4 993 vinyl H Et H H H H 4-MeC6H4 994 vinyl H Et H H H H 4-t-BuC6H4 995 vinyl H Et H H H H 1-Naph 996 vinyl H Et H H H H thiophene-2-yl 997 vinyl H Et H H H H pyridine-3-yl 998 vinyl H Et Me H H H 4-ClC6H4 999 vinyl H i-Pr H H H H Ph 1000 vinyl H i-Pr H H H H 4-ClC6H4 1001 vinyl H i-Pr H H H H 3,4-Cl2C6H3 1002 vinyl H i-Pr H H H H 2-MeC6H4 1003 vinyl H i-Pr H H H H 4-MeC6H4 1004 vinyl H i-Pr H H H H 4-EtC6H4 1005 vinyl H i-Pr H H H H 2-Naph 1006 vinyl H i-Pr H H H H thiophene-2-yl 1007 vinyl H i-Pr H H H H 5-methyl pyridine-3-yl 1008 vinyl H i-Pr Me H H H 4-MeC6H4 1009 vinyl H s-Bu H H H H 4-ClC6H4 1010 vinyl H s-Bu H H H H 3,4-Cl2C6H3 1011 vinyl H s-Bu H H H H 2-MeC6H4 1012 vinyl H s-Bu H H H H 4-MeC6H4 1013 vinyl H s-Bu H H H H 4-t-BuC6H4 1014 vinyl H s-Bu H H H H 1-Naph 1015 vinyl H s-Bu H H H H thiophene-2-yl 1016 vinyl H s-Bu H H H H isothiazole-5- yl 1017 vinyl H s-Bu Me H H H 4-MeC6H4 1018 vinyl H i-Bu H H H H 4-ClC6H4 1019 vinyl H i-Bu H Ph H H 3,4-Cl2C6H3 1020 vinyl H i-Bu H H H H 2-MeC6H4 1021 vinyl H i-Bu H H H H 4-MeC6H4 1022 vinyl H i-Bu H H H H 4-t-BuC6H4 1023 vinyl H i-Bu H H H H 1-Naph 1024 vinyl H i-Bu H H H H thiophene-2-yl 1025 vinyl H i-Bu H H H H isothiazole-5- yl 1026 vinyl H i-Bu Me H H H 4-MeC6H4 1027 vinyl H t-Bu H H H H Ph 1028 vinyl H t-Bu H H H H 4-ClC6H4 1029 vinyl H t-Bu H H H H 3,4-Cl2C6H3 1030 vinyl H t-Bu H H H H 2-MeC6H4 1031 vinyl H t-Bu H H H H 4-MeC6H4 1032 vinyl H t-Bu H H H H 4-t-BuC6H4 1033 vinyl H t-Bu H H H H 1-Naph 1034 vinyl H t-Bu H H H H Thiophene- 2-yl 1035 vinyl H t-Bu H H H H Isothiazole- 5-yl 1036 vinyl H t-Bu Me H H H 4-MeC6H4 1037 vinyl H Ph H H H H Ph 1038 vinyl H Ph H H H H 2-ClC6H4 1039 vinyl H Ph H H H H 4-ClC6H4 1040 vinyl H Ph H H H H 4-MeC6H4 1041 vinyl H Ph H H H H 4-EtC6H4 1042 4-MeC6H4CH2 H Me H H H H Ph 1043 4-MeC6H4CH2 H Me H H H H 2-BrC6H4 1044 4-MeC6H4CH2 H Me H H H H 3-BrC6H4 1045 4-MeC6H4CH2 H Me H H H H 4-BrC6H4 1046 4-MeC6H4CH2 H Me H H H H 4-MeC6H4 1047 4-MeC6H4CH2 H i-Pr H H H H 2-ClC6H4 1048 4-MeC6H4CH2 H i-Pr H H H H 3-ClC6H4 1049 4-MeC6H4CH2 H i-Pr H H H H 4-ClC6H4 1050 4-MeC6H4CH2 H i-Pr H H H H 4-MeC6H4 1051 4-MeC6H4CH2 H i-Pr H H H H 4-EtC6H4 1052 4-MeC6H4CH2 H i-Bu H H H H Ph 1053 4-MeC6H4CH2 H i-Bu H H H H 2-FC6H4 1054 4-MeC6H4CH2 H i-Bu H H H H 3-FC6H4 1055 4-MeC6H4CH2 H i-Bu H H H H 4-FC6H4 1056 4-MeC6H4CH2 H i-Bu H H H H 4-MeC6H4 1057 4-ClC6H4CH2 H Me H H H H Ph 1058 4-ClC6H4CH2 H Me H H H H 4-ClC6H4 1059 4-ClC6H4CH2 H Me H H H H 4-MeC6H4 1060 4-ClC6H4CH2 H Me H H H H thiophene-2-yl 1061 4-ClC6H4CH2 H Me H H H H pyridine-3-yl 1062 4-ClC6H4CH2 H i-Pr H H H H Ph 1063 4-ClC6H4CH2 H i-Pr H H H H 4-ClC6H4 1064 4-ClC6H4CH2 H i-Pr H H H H 3,4-Cl2C6H3 1065 4-ClC6H4CH2 H i-Pr H H H H 2-MeC6H4 1066 4-ClC6H4CH2 H i-Pr H H H H 4-MeC6H4 1067 4-ClC6H4CH2 H i-Bu H H H H Ph 1068 4-ClC6H4CH2 H i-Bu H H H H 2-MeC6H4 1069 4-ClC6H4CH2 H i-Bu H H H H 3-MeC6H4 1070 4-ClC6H4CH2 H i-Bu H H H H 4-MeC6H4 1071 4-ClC6H4CH2 H i-Bu Me H H H 1-Naph 1072 PhCH(CH3) H Me H H H H Ph 1073 PhCH(CH3) H Me H H H H 4-ClC6H4 1074 PhCH(CH3) H Me H H H H 4-MeC6H4 1075 PhCH(CH3) H Me H H H H thiophene-2-yl 1076 PhCH(CH3) H Me H H H H pyridine-4-yl 1077 PhCH(CH3) H i-Pr H H H H Ph 1078 PhCH(CH3) H i-Pr H H H H 4-ClC6H4 1079 PhCH(CH3) H i-Pr H H H H 3,4-Cl2C6H3 1080 PhCH(CH3) H i-Pr H H H H 2-MeC6H4 1081 PhCH(CH3) H i-Pr Me H H H 4-MeC6H4 1082 PhCH(CH3) H i-Bu H H H H Ph 1083 PhCH(CH3) H i-Bu H H H H 2-ClC6H4 1084 PhCH(CH3) H i-Bu H H H H 3-ClC6H4 1085 PhCH(CH3) H i-Bu H H H H 4-ClC6H4 1086 PhCH(CH3) H i-Bu H H H H 1-Naph 1087 PhCH(i-Pr) H Me H H H H Ph 1088 PhCH(i-Pr) H Me H H H H 4-ClC6H4 1089 PhCH(i-Pr) H Me H H H H 4-MeC6H4 1090 PhCH(i-Pr) H Me H H H H thiophene-2-yl 1091 PhCH(i-Pr) H Me H H H H pyridine-2-yl 1092 PhCH(i-Pr) H i-Pr H H H H Ph 1093 PhCH(i-Pr) H i-Pr H H H H 4-ClC6H4 1094 PhCH(i-Pr) H i-Pr H H H H 3,4-Cl2C6H3 1095 PhCH(i-Pr) H i-Pr H H H H 2-MeC6H4 1096 PhCH(i-Pr) H i-Pr H H H H 4-MeC6H4 1097 PhCH(i-Pr) H i-Bu H H H H Ph 1098 PhCH(i-Pr) H i-Bu H H H H 2-ClC6H4 1099 PhCH(i-Pr) H i-Bu H H H H 3-ClC6H4 1100 PhCH(i-Pr) H i-Bu H H H H 4-ClC6H4 1101 PhCH(i-Pr) H i-Bu H H H H 1-Naph 1102 PhC(CH3)2 H Me H H H H Ph 1103 PhC(CH3)2 H Me H H H H 4-ClC6H4 1104 PhC(CH3)2 H Me H H H H 4-MeC6H4 1105 PhC(CH3)2 H Me H H H H furan-2-yl 1106 PhC(CH3)2 H Me H H H H pyridine-4-yl 1107 PhC(CH3)2 H i-Pr H H H H Ph 1108 PhC(CH3)2 H i-Pr H H H H 4-ClC6H4 1109 PhC(CH3)2 H i-Pr H H H H 3,4-Cl2C6H3 1110 PhC(CH3)2 H i-Pr H H H H 2-MeC6H4 1111 PhC(CH3)2 H i-Pr H H H H 4-MeC6H4 1112 PhC(CH3)2 H i-Bu H H H H Ph 1113 PhC(CH3)2 H i-Bu H H H H 2-ClC6H4 1114 PbC(CH3)2 H i-Bu H H H H 3-ClC6H4 1115 PhC(CH3)2 H i-Bu H H H H 4-ClC6H4 1116 PhC(CH3)2 H i-Bu H H H H 2-Naph 1117 2-furylmethyl H Me H H H H Ph 1118 2-furylmethyl H Me H H H H 4-ClC6H4 1119 2-furylmethyl H Me H H H H 4-MeC6H4 1120 2-furylmethyl H Me H H H H thiophene-2-yl 1121 2-furylmethyl H Me H H H H pyridine-2-yl 1122 2-furylmethyl H i-Pr H H H H Ph 1123 2-furylmethyl H i-Pr H H H H 4-ClC6H4 1124 2-furylmethyl H i-Pr H H H H 3,4-Cl2C6H3 1125 2-furylmethyl H i-Pr H H H H 2-MeC6H4 1126 2-furylmethyl H i-Pr H H H H 4-MeC6H4 1127 2-furylmethyl H i-Bu H H H H Ph 1128 2-furylmethyl H i-Bu H H H H 2-ClC6H4 1129 2-furylmethyl H i-Bu H H H H 3-ClC6H4 1130 2-furylmethyl H i-Bu H H H H 4-ClC6H4 1131 2-furylmethyl H i-Bu H H H H 1-Naph 1132 3-furylmethyl H Me H H H H Ph 1133 3-furylmethyl H Me H H H H 4-ClC6H4 1134 3-furylmethyl H Me H H H H 4-MeC6H4 1135 3-furylmethyl H Me H H H H furan-2-yl 1136 3-furylmethyl H Me H H H H pyridine-4-yl 1137 3-furylmethyl H i-Pr H H H H Ph 1138 3-furylmethyl H i-Pr H H H H 4-ClC6H4 1139 3-furylmethyl H i-Pr H H H H 3,4-Cl2C6H3 1140 3-furylmethyl H i-Pr H H H H 2-MeC6H4 1141 3-furylmethyl H i-Pr H H H H 4-MeC6H4 1142 3-furylmethyl H i-Bu H H H H Ph 1143 3-furylmethyl H i-Bu H H H H 2-ClC6H4 1144 3-furylmethyl H i-Bu H H H H 3-ClC6H4 1145 3-furylmethyl H i-Bu H H H H 4-ClC6H4 1146 3-furylmethyl H i-Bu H H H H 2-Naph 1147 2-tetrahydrofurylmethyl H Me H H H H Ph 1148 2-tetrahydrofurylmethyl H Me H H H H 4-ClC6H4 1149 2-tetrahydrofurylmethyl H Me H H H H 4-MeC6H4 1150 2-tetrahydrofurylmethyl H Me H H H H thiophene-2-yl 1151 2-tetrahydrofurylmethyl H Me H H H H pyridine-2-yl 1152 2-tetrahydrofurylmethyl H i-Pr H H H H Ph 1153 2-tetrahydrofurylmethyl H i-Pr H H H H 4-ClC6H4 1154 2-tetrahydrofurylmethyl H i-Pr H H H H 3,4-Cl2C6H3 1155 2-tetrahydrofurylmethyl H i-Pr H H H H 2-MeC6H4 1156 2-tetrahydrofurylmethyl H i-Pr H H H H 4-MeC6H4 1157 2-tetrahydrofurylmethyl H i-Bu H H H H Ph 1158 2-tetrahydrofurylmethyl H i-Bu H H H H 2-ClC6H4 1159 2-tetrahydrofurylmethyl H i-Bu H H H H 3-ClC6H4 1160 2-tetrahydrofurylmethyl H i-Bu H H H H 4-ClC6H4 1161 2-tetrahydrofurylmethyl H i-Bu H H H H 1-Naph 1162 2-thienylmethyl H Me H H H H Ph 1163 2-thienylmethyl H Me H H H H 4-ClC6H4 1164 2-thienylmethyl H Me H H H H 4-MeC6H4 1165 2-thienylmethyl H Me H H H H thiophene-2-yl 1166 2-thienylmethyl H Me H H H H pyridine-2-yl 1167 2-thienylmethyl H i-Pr H H H H Ph 1168 2-thienylmethyl H i-Pr H H H H 4-ClC6H4 1169 2-thienylmethyl H i-Pr H H H H 3,4-Cl2C6H3 1170 2-thienylmethyl H i-Pr H H H H 2-MeC6H4 1171 2-thienylmethyl H i-Pr H H H H 4-MeC6H4 1172 2-thienylmethyl H i-Bu H H H H Ph 1173 2-thienylmethyl H i-Bu H H H H 2-ClC6H4 1174 2-thienylmethyl H i-Bu H H H H 3-ClC6H4 1175 2-thienylmethyl H i-Bu H H H H 4-ClC6H4 1176 2-thienylmethyl H i-Bu H H H H 1-Naph 1177 cyclopropylmethyl H Me H H H H Ph 1178 cyclopropylmethyl H Me H H H H 4-ClC6H4 1179 cyclopropylmethyl H Me H H H H 4-MeC6H4 1180 cyclopropylmethyl H Me H H H H furan-2-yl 1181 cyclopropylmethyl H Me H H H H pyridine-4-yl 1182 cyclopropylmethyl H i-Pr H H H H Ph 1183 cyclopropylmethyl H i-Pr H H H H 4-ClC6H4 1184 cyclopropylmethyl H i-Pr H H H H 3,4-Cl2C6H3 1185 cyclopropylmethyl H i-Pr H H H H 2-MeC6H4 1186 cyclopropylmethyl H i-Pr H H H H 4-MeC6H4 1187 cyclopropylmethyl H i-Bu H H H H Ph 1188 cyclopropylmethyl H i-Bu H H H H 2-ClC6H4 1189 cyclopropylmethyl H i-Bu H H H H 3-ClC6H4 1190 cyclopropylmethyl H i-Bu H H H H 4-ClC6H4 1191 cyclopropylmethyl H i-Bu H H H H 2-Naph 1192 neopentyl H Me H H H H Ph 1193 neopentyl H Me H H H H 4-ClC6H4 1194 neopentyl H Me H H H H 4-MeC6H4 1195 neopentyl H Me H H H H thiophene-2-yl 1196 neopentyl H Me H H H H pyridine-2-yl 1197 neopentyl H i-Pr H H H H Ph 1198 neopentyl H i-Pr H H H H 4-ClC6H4 1199 neopentyl H i-Pr H H H H 3,4-Cl2C6H3 1200 neopentyl H i-Pr H H H H 2-MeC6H4 1201 neopentyl H i-Pr H H H H 4-MeC6H4 1202 neopentyl H i-Bu H H H H Ph 1203 neopentyl H i-Bu H H H H 2-ClC6H4 1204 neopentyl H i-Bu H H H H 3-ClC6H4 1205 neopentyl H i-Bu H H H H 4-ClC6H4 1206 neopentyl H i-Bu H H H H 1-Naph 1207 methallyl H Me H H H H Ph 1208 methallyl H Me H H H H 4-ClC6H4 1209 methallyl H Me H H H H 4-MeC6H4 1210 methallyl H Me H H H H furan-2-yl 1211 methallyl H Me H H H H pyridine-4-yl 1212 methallyl H i-Pr H H H H Ph 1213 methallyl H i-Pr H H H H 4-ClC6H4 1214 methallyl H i-Pr H H H H 3,4-Cl2C6H3 1215 methallyl H i-Pr H H H H 2-MeC6H4 1216 methallyl H i-Pr H H H H 4-MeC6H4 1217 methallyl H i-Bu H H H H Ph 1218 methallyl H i-Bu H H H H 2-ClC6H4 1219 methallyl H i-Bu H H H H 3-ClC6H4 1220 methallyl H i-Bu H H H H 4-ClC6H4 1221 methallyl H i-Bu H H H H 2-Naph 1222 1,2-dimethylpropyl H Me H H H H Ph 1223 1,2-dimethylpropyl H Me H H H H 4-ClC6H4 1224 1,2-dimethylpropyl H Me H H H H 4-MeC6H4 1225 1,2-dimethylpropyl H Me H H H H thiophene-2-yl 1226 1,2-dimethylpropyl H Me H H H H pyridine-2-yl 1227 1,2-dimethylpropyl H i-Pr H H H H Ph 1228 1,2-dimethylpropyl H i-Pr H H H H 4-ClC6H4 1229 1,2-dimethylpropyl H i-Pr H H H H 3,4-Cl2C6H3 1230 1,2-dimethylpropyl H i-Pr H H H H 2-MeC6H4 1231 1,2-dimethylpropyl H i-Pr H H H H 4-MeC6H4 1232 1,2-dimethylpropyl H i-Bu H H H H Ph 1233 1,2-dimethylpropyl H i-Bu H H H H 2-ClC6H4 1234 1,2-dimethylpropyl H i-Bu H H H H 3-ClC6H4 1235 1,2-dimethylpropyl H i-Bu H H H H 4-ClC6H4 1236 1,2-dimethylpropyl H i-Bu H H H H 1-Naph 1237 4-MeOC6H4CH2 H Me H H H H Ph 1238 4-MeOC6H4CH2 H Me H H H H 4-ClC6H4 1239 4-MeOC6H4CH2 H Me H H H H 4-MeC6H4 1240 4-MeOC6H4CH2 H Me H H H H furan-2-yl 1241 4-MeOC6H4CH2 H Me H H H H pyridine-4-yl 1242 4-MeOC6H4CH2 H i-Pr H H H H Ph 1243 4-MeOC6H4CH2 H i-Pr H H H H 4-ClC6H4 1244 4-MeOC6H4CH2 H i-Pr H H H H 3,4-Cl2C6H3 1245 4-MeOC6H4CH2 H i-Pr H H H H 2-MeC6H4 1246 4-MeOC6H4CH2 H i-Pr H H H H 4-MeC6H4 1247 4-MeOC6H4CH2 H i-Bu H H H H Ph 1248 4-MeOC6H4CH2 H i-Bu H H H H 2-ClC6H4 1249 4-MeOC6H4CH2 H i-Bu H H H H 3-ClC6H4 1250 4-MeOC6H4CH2 H i-Bu H H H H 4-ClC6H4 1251 4-MeOC6H4CH2 H i-Bu H H H H 2-Naph 1252 2-(methylthio)ethyl H Me H H H H Ph 1253 2-(methylthio)ethyl H Me H H H H 4-ClC6H4 1254 2-(methylthio)ethyl H Me H H H H 4-MeC6H4 1255 2-(methylthio)ethyl H Me H H H H thiophene-2-yl 1256 2-(methylthio)ethyl H Me H H H H pyridine-2-yl 1257 2-(methylthio)ethyl H i-Pr H H H H Ph 1258 2-(methylthio)ethyl H i-Pr H H H H 4-ClC6H4 1259 2-(methylthio)ethyl H i-Pr H H H H 3,4-Cl2C6H3 1260 2-(methylthio)ethyl H i-Pr H H H H 2-MeC6H4 1261 2-(methylthio)ethyl H i-Pr H H H H 4-MeC6H4 1262 2-(methylthio)ethyl H i-Bu H H H H Ph 1263 2-(methylthio)ethyl H i-Bu H H H H 2-ClC6H4 1264 2-(methylthio)ethyl H i-Bu H H H H 3-ClC6H4 1265 2-(methylthio)ethyl H i-Bu H H H H 4-ClC6H4 1266 2-(methylthio)ethyl H i-Bu H H H H 1-Naph 1267 2-(methanesulfonyl)ethyl H Me H H H H Ph 1268 2-(methanesulfonyl)ethyl H Me H H H H 4-ClC6H4 1269 2-(methanesulfonyl)ethyl H Me H H H H 4-MeC6H4 1270 2-(methanesulfonyl)ethyl H Me H H H H furan-2-yl 1271 2-(methanesulfonyl)ethyl H Me H H H H pyridine-4-yl 1272 2-(methanesulfonyl)ethyl H i-Pr H H H H Ph 1273 2-(methanesulfonyl)ethyl H i-Pr H H H H 4-ClC6H4 1274 2-(methanesulfonyl)ethyl H i-Pr H H H H 3,4-Cl2C6H3 1275 2-(methanesulfonyl)ethyl H i-Pr H H H H 2-MeC6H4 1276 2-(methanesulfonyl)ethyl H i-Pr H H H H 4-MeC6H4 1277 2-(methanesulfonyl)ethyl H i-Bu H H H H Ph 1278 2-(methanesulfonyl)ethyl H i-Bu H H H H 2-ClC6H4 1279 2-(methanesulfonyl)ethyl H i-Bu H H H H 3-ClC6H4 1280 2-(methanesulfonyl)ethyl H i-Bu H H H H 4-ClC6H4 1281 2-(methanesulfonyl)ethyl H i-Bu H H H H 2-Naph 1282 2-thienyl H Me H H H H Ph 1283 2-thienyl H Me H H H H 4-ClC6H4 1284 2-thienyl H Me H H H H 4-MeC6H4 1285 2-thienyl H Me H H H H thiophene-2-yl 1286 2-thienyl H Me H H H H pyridine-2-yl 1287 2-thienyl H i-Pr H H H H Ph 1288 2-thienyl H i-Pr H H H H 4-ClC6H4 1289 2-thienyl H i-Pr H H H H 3,4-Cl2C6H3 1290 2-thienyl H i-Pr H H H H 2-MeC6H4 1291 2-thienyl H i-Pr H H H H 4-MeC6H4 1292 2-thienyl H i-Bu H H H H Ph 1293 2-thienyl H i-Bu H H H H 2-ClC6H4 1294 2-thienyl H i-Bu H H H H 3-ClC6H4 1295 2-thienyl H i-Bu H H H H 4-ClC6H4 1296 2-thienyl H i-Bu H H H H 1-Naph

TABLE 2 Analytical data Comp. No. Analytical data 4 ¹HNMR(CDCl₃, ppm): 1.15(3H, d, J=6.1Hz), 3.46-3.61(2H, m), 3.63(3H, s), 3.66-3.72(1H, m), 4.86(1H, d, J=8.5Hz), 6.86(1H, br-s), 7.41(2H, d, J=8.1Hz), 7.74(2H, d, J=8.1Hz). 26 ¹HNMR(CDCl₃, ppm): 1.00(6H, t, J=8.1Hz), 1.85-1.89(1H, m), 3.46-3.61(2H, m), 3.63(3H, s), 3.66-3.72(1H, m), 4.86(1H, d, J=8.5Hz), 6.86(1H, br-s), 7.39-7.49 (3H, m), 7.79(2H, d, J=7.1Hz). 30 ¹HNMR(CDCl₃, ppm): 1.00(6H, t, J=8.1Hz), 1.85-1.89(1H, m), 2.39(3H, s), 3.46-3.61(2H, m), 3.63(3H, s), 3.66-3.72(1H, m), 4.86(1H, d, J=8.5Hz), 6.86(1H, br-s), 7.23(2H, d, J=8.1Hz), 7.68(2H, d, J=8.1Hz). 66 ¹HNMR(CDCl₃, ppm): 3.46-3.61(2H, m), 3.63(3H, s), 3.66-3.72(1H, m), 4.86(1H, d, J=8.5Hz), 6.86(1H, br-s), 7.23-7.41(5H, m), 7.39-7.49(3H, m), 7.79 1(2H, d, J=7.1Hz). 215 ¹HNMR(CDCl₃, ppm): 1.14(3H, d, J=6.1Hz), 1.22(3H, d, J=6.8Hz), 1.24(3H, d, J=6.8Hz), 2.39(3H, s), 3.48-3.53(2H, m), 3.96-3.99(1H, m), 4.79(1H, br-s), 4.84-4.91(1H, m), 7.23(2H, d, J=8.1Hz), 7.70(2H, d, J=8.1Hz). 216 ¹HNMR(CDCl₃, ppm): 1.14(3H, d, J=6.1Hz), 1.22(3H, d, J=6.8Hz), 1.24(3H, d, J=6.8Hz), 1.32(9H, s), 3.48-3.53(2H, m), 3.96-3.99(1H, m), 4.79(1H, br-s), 4.84-4.91(1H, m), 7.23(2H, d, J=8.1Hz), 7.70(2H, d, J=8.1Hz). 236 ¹HNMR(CDCl₃, ppm): 1.01(6H, t, J=7.1Hz), 1.09(3H, d, J=6.1Hz), 1.22(3H, d, J=6.1Hz), 1.85-1.89(1H, m), 3.48-3.61(2H, m), 3.68-3.74(1H, m), 4.12(1H, d, J=7.3Hz), 4.73-4.89(1H, m), 7.06(1H, br-s), 7.40-7.50(3H, m), 7.80(2H, d, J=7.1Hz). 237 ¹HNMR(CDCl₃, ppm): 1.00(3H, d, J=6.8Hz), 1.01(3H, d, J=6.8Hz), 1.11(3H, d, J=6.1Hz), 1.23(3H, d, J=6.1Hz), 1.85-1.90(1H, m), 3.50-3.54(2H, m), 3.67-3.73 (1H, m), 4.73(1H, d, J=8.8Hz), 4.83-4.90(1H, m), 7.21(1H, br-s), 7.40(2H, d, J=8.5Hz), 7.75(2H, d, J=8.5Hz). 238 ¹HNMR(CDCl₃, ppm): 1.01(6H, t, J=6.8Hz), 1.14(3H, d, J=6.3Hz), 1.24(3H, d, J=6.3Hz), 1.85-1.90(1H, m), 3.50-3.53(2H, m), 3.67-3.72(1H, m), 4.75(1H, d, J=8.3Hz), 4.86-4.92(1H, m), 7.35(1H, br-s), 7.50(1H, d, J=8.3Hz), 7.62(1H, d, J=8.3Hz), 7.94(1H, s). 239 ¹HNMR(CDCl₃, ppm): 0.98(3H, d, J=6.8Hz), 1.00(3H, d, J=6.8Hz), 1.17(3H, d, J=6.3Hz), 1.21(3H, d, J=6.3Hz), 1.83-1.88(1H, m), 2.44(3H, s), 3.41-3.47(1H, m), 3.56-3.70(2H, m), 4.77(1H, d, J=8.5Hz), 4.82-4.88(1H, m), 6.29(1H br-s), 7.16-7.35(4H, m). 240 ¹HNMR(CDCl₃, ppm): 0.99(3H, d, J=7.3Hz), 1.01(3H, d, J=7.3Hz), 1.10(3H, d, J=6.1Hz), 1.21(3H, d, J=6.1Hz), 1.84-1.88(1H, m), 2.38(3H, s), 3.47-3.60(2H, m), 3.67-3.73(1H, m), 4.75(1H, d, J=8.5Hz), 4.83-4.89(1H, m), 6.99(1H, br-s), 7.22 (2H, d, J=8.1Hz), 7.69(2H, d, J=8.1Hz). 241 ¹HNMR(CDCl₃, ppm): 1.00(6H, t, J=7.3Hz), 1.09(3H, d, J=6.2Hz), 1.21-1.26(6H, m), 1.82-1.90(1H, m), 2.68(2H, q, J=7.6Hz), 3.46-3.62(2H, m), 3.68-3.76(1H, m), 4.74(1H, d, J=8.8Hz), 4.87-4.90(1H, m), 6.99(1H, d, J=8.1Hz), 7.24(2H, d, J=8.5Hz), 7.72(2H, d, J=8.5Hz). 242 ¹HNMR(CDCl₃, ppm): 1.03(6H, t, J=6.8Hz), 1.09(3H, d, J=6.1Hz), 1.22(3H, d, J=6.1Hz), 1.87-1.92(1H, m), 3.54-3.67(2H, m), 3.74-3.78(1H, m), 4.77(1H, d, J=8.5Hz), 4.86-4.92(1H, m), 7.23(1H, br-s), 7.51-7.58(2H, m), 7.86-7.94(4H, m), 8.34(1H, s). 243 ¹HNMR(CDCl₃, ppm): 0.97-1.00(6H, m), 1.11(3H, d, J=6.3Hz), 1.22(3H, d, J=6.3Hz), 1.80-1.90(1H, m), 2.50(3H, s), 3.44-3.57(2H, m), 3.66-3.73(1H, m), 4.76(1H, d, J=8.5Hz), 4.87-4.90(1H, m), 6.71(1H, d, J=3.7Hz), 6.87(1H, br-s), 7.30(1H, d, J=3.7Hz) 245 ¹HNMR(CDCl₃, ppm): 0.93(3H, d, J=7.1Hz), 0.95(3H, d, J=7.1Hz), 1.15(3H, s), 1.23(6H, d, J=6.3Hz), 2.35-2.40(4H, m), 3.60(1H, dd, J=5.1Hz, 14.2Hz), 3.82 (1H, dd, J=5.9Hz, 14.2Hz), 4.72(1H, br-s), 4.87-4.93(1H, m), 7.24(2H, d, J=8.1Hz), 7.76(2H, d, J=8.1Hz). 246 ¹HNMR(CDCl₃, ppm): 1.00-1.03(6H, m), 1.17(3H, d, J=6.6Hz), 1.26(6H, d, J=6.3Hz), 1.65-1.69(1H, m), 2.39(3H, s), 3.51-3.56(1H, m), 4.33-4.37(1H, m), 4.56(1H, d, J=8.0Hz), 4.92-5.00(1H, m), 7.23(2H, d, J=8.3Hz), 7.30(1H, br-s), 7.72(2H, d, J=8.3Hz). 247 ¹HNMR(CDCl₃, ppm): 0.99-1.03(6H, m), 1.18(3H, d, J=6.6Hz), 1.26(6H, d, J=6.3Hz), 1.62-1.67(1H, m), 3.50-3.54(1H, m), 4.33-4.35(1H, m), 4.53(1H, d, J=8.0Hz), 4.91-4.98(1H, m), 7.22(2H, d, J=8.3Hz), 7.31(1H, br-s), 7.74(2H, d, J=8.3Hz). 279 ¹HNMR(CDCl₃, ppm): 1.15-1.26(6H, m), 2.40(3H, s), 3.25-3.30(1H, m), 3.42-3.50 (1H, m), 4.82-4.90(1H, m), 4.92-4.98(1H, m), 5.60(1H, d, J=7.1Hz), 6.84(1H, br-s), 7.22-7.40(7H, m), 7.67(2H, d, J=7.8Hz). 284 ¹HNMR(CDCl₃, ppm): 1.13-1.19(6H, m), 2.40(3H, m), 3.70-3.80(2H, m), 4.82-4.92 (2H, m), 5.80(1H, d, J=7.1Hz), 6.65(1H, br-s), 7.21-7.29(4H, m), 7.34(2H, d, J=8.1Hz), 7.65(2H, d, J=8.1Hz). M⁺: 375. 289 ¹HNMR(CDCl₃, ppm): 1.12(3H, d, J=6.1Hz), 1.18(3H, d, J=6.1Hz), 2.38(3H, s), 2.80-2.86(1H, m), 2.92-2.98(1H, m), 3.49-3.56(2H, m), 4.07-4.15(1H, m), 4.81-4.88(1H, m), 4.95(1H, d, J=7.3Hz), 6.88(1H, br-s), 7.20-7.27(5H, m), 7.31 (2H, d, J=8.1Hz), 7.65(2H, d, J=8.1Hz). 290 ¹HNMR(CDCl₃, ppm): 1.12(3H, d, J=6.1Hz), 1.18(3H, d, J=6.1Hz), 1.20-1.25(3H, m), 2.67(2H, q, J=7.6Hz), 2.80-2.86(1H, m), 2.92-2.98(1H, m), 3.49-3.56(2H, m), 4.07-4.15(1H, m), 4.81-4.88(1H, m), 4.95(1H, d, J=7.3Hz), 6.88(1H, br-s), 7.20-7.27(5H, m), 7.31(2H, d, J=8.1Hz), 7.65(2H, d, J=8.1Hz). 384 ¹HNMR(CDCl₃, ppm): 0.85(3H, d, J=6.6Hz), 0.86(3H, d, J=6.6Hz), 1.01(6H, t, J=6.6Hz), 1.79-1.89(1H, m), 3.47-3.71(3H, m), 3.80(2H, d, J=6.8Hz), 4.82(1H, d, J=8.3Hz), 6.92(br-s), 7.41(2H, d, J=8.3Hz), 7.76(2H, d, J=8.3Hz). 387 ¹HNMR(CDCl₃, ppm): 0.84(3H, d, J=6.8Hz), 0.85(3H, d, J=6.8Hz), 1.06(6H, d, J=6.8Hz), 1.63-1.89(2H, m), 2.39(3H, s), 3.46-3.74(3H, m), 3.80(2H, d, J=6.6Hz), 4.82(1H, d, J=8.8Hz), 6.92(1H, br-s), 7.22(2H, d, J=7.8Hz), 7.68(2H, d, J=7.8Hz). 464 ¹HNMR(CDCl₃, ppm): 1.00(6H, t, J=6.8Hz), 1.39(9H, s), 1.82-1.87(1H, m), 2.38 (3H, s), 3.46-3.53(2H, m), 3.65-3.69(1H, m), 4.65(1H, d, J=8.5Hz), 7.04(1H, br-s), 7.21(2H, d, J=8.1Hz), 7.70(2H, d, J=8.1Hz). 469 ¹HNMR(CDCl₃, ppm): 0.92(3H, d, J=6.8Hz), 0.94(3H, d, J=6.8Hz), 1.13(3H, s), 2.37-2.41(4H, m), 3.57(1H, dd, J=5.6Hz), 13.7Hz), 3.81(1H, dd, J=5.6Hz), 13.7Hz), 4.62(1H, br-s), 7.24(2H, d, J=8.1Hz), 7.77(2H, d, J=8.1Hz), 8.17(1H, br-s). 470 ¹HNMR(CDCl₃, ppm): 1.00-1.03(6H, m), 1.17(3H, d, J=6.6Hz), 1.49(9H, s), 1.58-1.67(1H, m), 3.47-3.53(1H, m), 4.33-4.35(1H, m), 4.51(1H, d,, J=8.0Hz), 7.23(2H, d, J=8.3Hz), 7.38(1H, br-s), 7.73(2H, d, J=8.3Hz). 471 ¹HNMR(CDCl₃, ppm): 1.00-1.03(6H, m), 1.16(3H, d, J=6.6Hz), 1.49(9H, s), 1.59-1.68(1H, m), 2.38(3H, s), 3.46-3.52(1H, m), 4.33-4.35(1H, m), 4.51(1H, d, J=8.0Hz), 7.21(2H, d, J=8.3Hz), 7.36(1H, br-s), 7.72(2H, d, J=8.3Hz). 504 ¹HNMR(CDCl₃, ppm): 1.40(9H, s), 2.40(3H, s), 3.25-3.30(1H, m), 3.42-3.50(1H, m), 4.82-4.90(1H, m), 5.60(1H, d, J=7.1Hz), 6.84(1H, br-s), 7.22-7.40(7H, m), 7.67(2H, d, J=7.8Hz). 526 ¹HNMR(CDCl₃, ppm): 1.05(3H, d, J=6.8Hz), 1.07(3H, d, J=6.8Hz), 1.91-1.96 (1H, m), 2.40(3H, s), 3.47-3.50(1H, m), 3.74-3.78(2H, m), 5.26(1H, d, J=7.6Hz), 6.76(1H, br-s), 7.15-7.31(5H, m), 7.40-7.50(3H, m), 7.80(2H, d, J=7.3Hz). 530 ¹HNMR(CDCl₃, ppm): 1.05(3H, d, J=6.8Hz), 1.07(3H, d, J=6.8Hz), 1.91-1.96 (1H, m), 2.40(3H, s), 3.47-3.50(1H, m), 3.74-3.78(2H, m), 5.26(1H, d, J=7.6Hz), 6.76(1H, br-s), 6.95(2H, d, J=8.3Hz), 7.15-7.31(5H, m), 7.68(2H, d, J=8.3Hz). 596 ¹HNMR(CDCl₃, ppm): 0.99(3H, d, J=6.8Hz), 1.01(3H, d, J=6.8Hz), 1.85-1.90 (1H, m), 2.39(3H, s), 3.48-3.62(2H, m), 3.69-3.74(1H, m), 4.94(1H, d, J=8.8Hz), 5.06(2H, d, J=7.1Hz), 6.86(1H, br-s), 7.20-7.30(7H, m), 7.41-7.51(3H, m), 7.79(2H, d, J=7.1Hz). 600 ¹HNMR(CDCl₃, ppm): 0.99(3H, d, J=6.8Hz), 1.01(3H, d, J=6.8Hz), 1.85-1.90 (1H, m), 2.39(3H, s), 3.48-3.62(2H, m), 3.69-3.74(1H, m), 4.94(1H, d, J=8.8Hz), 5.06(2H, d, J=7.1Hz), 6.86(1H, br-s), 7.20-7.30(7H, m), 7.65(2H, d, J=8.1Hz). 636 ¹HNMR(CDCl₃, ppm): 3.48-3.62(2H, m), 3.69-3.74(1H, m), 4.94(1H, d, J=8.8Hz), 5.06(2H, d, J=7.1Hz), 6.86(1H, br-s), 7.20-7.40(14H, m), 7.82(2H, d, J=7.1Hz). 674 ¹HNMR(CDCl₃, ppm): 1.10(3H, d, J=6.8Hz), 1.12(3H, d, J=6.8Hz), 1.94-2.01 (1H, m), 3.50-3.55(1H, m), 3.80-3.84(2H, m), 5.31(1H, d, J=8.5Hz), 6.78(1H, br-s), 7.10(1H, d, J=8.8Hz), 7.21(2H, d, J=7.8Hz), 7.37(1H, s), 7.41-7.56(2H, m), 7.60-7.90(5H, m). 677 ¹HNMR(CDCl₃, ppm): 1.09(3H, d, J=6.8Hz), 1.10(3H, d, J=6.8Hz), 1.94-1.99 (1H, m), 2.40(3H, s), 3.47-3.51(1H, m), 3.80-3.84(2H, m), 5.30(1H, d, J=8.5Hz), 6.77(1H, br-s), 7.10(1H, d, J=8.8Hz), 7.21(2H, d, J=7.8Hz), 7.34(1H, s), 7.41-7.54(2H, m), 7.63-7.93(5H, m). 739 ¹HNMR(CDCl₃, ppm): 1.00(6H, t, J=7.3Hz), 1.85-1.90(1H, m), 3.46-3.74(3H, m), 4.52(2H, d, J=5.6Hz), 4.93(1H, d, J=8.3Hz), 5.14(1H, d, J=10.5Hz), 5.25 (1H, d, J=17.1Hz), 4.79-5.88(1H, m), 6.88(1H, br-s), 7.39(2H, d, J=8.1Hz), 7.73(2H, d, J=8.1Hz). 742 ¹HNMR(CDCl₃, ppm): 1.00(6H, t, J=7.3Hz), 1.85-1.90(1H, m), 2.39(3H, s), 3.46-3.74(3H, m), 4.52(2H, d, J=5.6Hz), 4.93(1H, d, J=8.3Hz), 5.14(1H, d, J=10.5Hz), 5.25(1H, d, J=17.1Hz), 4.79-5.88(1H, m), 6.88(1H, br-s), 7.22(2H, d, J=8.1Hz), 7.68(2H, d, J=8.1Hz). 804 ¹HNMR(CDCl₃, ppm): 1.00(6H, t, J=7.8Hz), 1.86-1.91(1H, m), 2.36(1H, s), 3.47-3.74(3H, m), 4.63(2H, s), 5.01(1H, d, J=9.0Hz), 6.79(1H, br-s), 7.38(2H, d, J=8.1Hz), 7.73(2H, d, J=8.1Hz). 807 ¹HNMR(CDCl₃, ppm): 1.00(6H, t, J=7.8Hz), 1.86-1.91(1H, m), 2.36(1H, s), 2.39 (3H, s), 3.47-3.74(3H, m), 4.63(2H, s), 5.01(1H, d, J=9.0Hz), 6.79(1H, br-s), 7.22 (2H, d, J=8.1Hz), 7.68(2H, d, J=8.1Hz). 1049 ¹HNMR(CDCl₃, ppm): 0.98(3H, d, J=7.1Hz), 1.00(3H, d, J=7.1Hz), 1.84-1.89(1H, m), 2.31(3H, s), 3.49-3.57(2H, m), 3.69-3.75(1H, m), 4.92(1H, d, J=9.0Hz), 5.00 (1H, d, J=12.2Hz), 5.05(1H, d, J=12.2Hz), 7.00(1H, br-s), 7.07(2H, d, J=8.1Hz), 7.16(2H, d, J=7.8Hz), 7.24(2H, d, J=8.1Hz), 7.67(2H, d, J=7.8Hz). 1050 ¹HNMR(CDCl₃, ppm): 0.98(3H, d, J=7.1Hz), 1.00(3H, d, J=7.1Hz), 1.84-1.89(1H, m), 2.31(3H, s), 2.40(3H, s), 3.49-3.57(2H, m), 3.69-3.75(1H, m), 4.92(1H, d, J=9.0Hz), 5.00(1H, d, J=12.2Hz), 5.05(1H, d, J=12.2Hz), 7.00(1H, br-s), 7.07 (2H, d, J=8.1Hz), 7.16(2H, d, J=7.8Hz), 7.22(2H, d, J=8.1Hz), 7.65(2H, d, J=7.8Hz). 1063 ¹HNMR(CDCl₃, ppm): 1.00(6H, t, J=7.1Hz), 1.83-1.90(1H, m), 3.43-3.47(1H, m), 3.62-3.73(2H, m), 4.94(1H, d, J=12.4Hz), 4.95(1H, d, J=9.0Hz), 5.06(1H, d, J=12.4Hz), 6.73(1H, br-s), 7.17-7.22(6H, m), 7.59(2H, d, J=8.1Hz). 1066 ¹HNMR(CDCl₃, ppm): 1.00(6H, t, J=7.1Hz), 1.83-1.90(1H, m), 2.41(3H, s), 3.43-3.47(1H, m), 3.62-3.73(2H, m), 4.94(1H, d, J=12.4Hz), 4.95(1H, d, J=9.0Hz), 5.06(1H, d, J=12.4Hz), 6.73(1H, br-s), 7.17-7.22(6H, m), 7.61(2H, d, J=8.1Hz). 1078 ¹HNMR(CDCl₃, ppm): 0.95-1.02(6H, m), 1.39(3×1/2H, d, J=6.6Hz), 1.51(3H×1/2, d, J=6.6Hz), 1.80-1.88(1H, m), 3.40-3.64(3H, m), 4.90(1H×1/2, d, J=8.5Hz), 4.96(1H×1/2, d, J=9.0Hz), 5.70-5.77(1H, m), 6.71(1H×1/2, br-s), 6.78(1H×1/2, br-s), 7.09-7.36(6H, m), 7.45(2H×1/2, d, J=8.3Hz), 7.69(2H×1/2, d, J=8.3Hz). 1081 ¹HNMR(CDCl₃, ppm): 0.95-1.02(6H, m), 1.39(3H×1/2, d, J=6.6Hz), 1.51(3H×1/2, d, J=6.6Hz), 1.80-1.88(1H, m), 2.37(3H×1/2, s), 2.40(3H×1/2, s), 3.40-3.64(3H, m), 4.90(1H×1/2, d, J=8.5Hz), 4.96(1H×1/2, d, J=9.0Hz), 5.70-5.77(1H, m), 6.71(1H×1/2, br-s), 6.78(1H×1/2, br-s), 7.09-7.36(6H, m), 7.47(2H×1/2, d, J=8.3Hz), 7.71(2H×1/2, d, J=8.3Hz). 1123 ¹HNMR(CDCl₃, ppm): 0.99(3H, d, J=6.8Hz), 1.02(3H, d, J=6.8Hz), 1.85-1.89(1H, m), 3.51-3.54(2H, m), 3.72-3.76(1H, m), 4.90(1H, d, J=9.0Hz), 5.02(2H, d, J=4.9Hz), 6.29(1H, d, J=3.2Hz), 6.31(1H, d, J=3.2Hz), 6.85(1H, br-s), 7.20(2H, d, J=8.1Hz), 7.33(1H, s), 7.66(2H, d, J=8.1Hz). 1126 ¹HNMR(CDCl₃, ppm): 0.98(3H, d, J=6.8Hz), 1.00(3H, d, J=6.8Hz), 1.85-1.89(1H, m), 2.40(3H, s), 3.51-3.54(2H, m), 3.70-3.76(1H, m), 4.90(1H, d, J=9.0Hz), 5.02 (2H, d, J=4.9Hz), 6.29(1H, d, J=3.2Hz), 6.33(1H, d, J=3.2Hz), 6.87(1H, br-s), 7.23(2H, d, J=8.1Hz), 7.33(1H, s), 7.68(2H, d, J=8.1Hz). 1138 ¹HNMR(CDCl₃, ppm): 0.98(3H, d, J=6.8Hz), 1.00(3H, d, J=6.8Hz), 1.84-1.89(1H, m), 3.48-3.61(2H, m), 3.68-3.73(1H, m), 4.88(1H, d, J=6.8Hz), 4.92(2H, s), 6.34 (1H, s), 6.80(1H, br-s), 7.20(2H, d, J=7.8Hz), 7.29(1H, d, J=2.0Hz), 7.41(1H, d, J=2.0Hz), 7.63(2H, d, J=7.8Hz). 1141 ¹HNMR(CDCl₃, ppm): 0.98(3H, d, J=6.8Hz), 1.00(3H, d, J=6.8Hz), 1.84-1.89(1H, m), 2.40(3H, s), 3.48-3.61(2H, m), 3.68-3.73(1H, m), 4.88(1H, d, J=6.8Hz), 4.92 (2H, s), 6.33(1H, s), 6.83(1H, br-s), 7.22(2H, d, J=7.8Hz), 7.31(1H, d, J=2.0Hz), 7.39(1H, d, J=2.0Hz), 7.65(2H, d, J=7.8Hz). 1153 ¹HNMR(CDCl₃, ppm): 1.00(3H, d, J=6.8Hz), 1.01(3H, d, J=6.8Hz), 1.49-1.56(1H, m), 1.81-1.95(4H, m), 3.51-3.54(2H, m), 3.65-4.16(6H, m), 4.95(1H, d, J=8.5Hz), 6.91(1H, br-s), 7.24(2H, d, J=8.1Hz), 7.70(2H, d, J=8.1Hz). 1156 ¹HNMR(CDCl₃, ppm): 0.99(3H, d, J=6.8Hz), 1.01(3H, d, J=6.8Hz), 1.49-1.56(1H, m), 1.81-1.95(4H, m), 2.39(3H, s), 3.51-3.55(2H, m), 3.67-4.16(6H, m), 4.95(1H, d, J=8.5Hz), 6.93(1H, br-s), 7.22(2H, d, J=8.1Hz), 7.68 (2H, d, J=8.1Hz). 1168 ¹HNMR(CDCl₃, ppm): 0.98(3H, d, J=6.8Hz), 1.00(3H, d, J=6.8Hz), 1.85-1.89(1H, m), 3.51-3.56(2H, m), 3.70-3.75(1H, m), 4.91(1H, d, J=8.8Hz), 5.19(1H, d, J=12.7Hz), 5.22(1H, d, J=12.7Hz), 6.83(1H, br-s), 6.91(1H, dd, J=1.7Hz, 3.4Hz), 7.01 (1H, dd, J=1.7Hz, 3.4Hz), 7.21-7.25(3H, m), 7.68(2H, d, J=8.1Hz). 1171 ¹HNMR(CDCl₃, ppm): 0.98(3H, d, J=6.8Hz), 1.00(3H, d, J=6.8Hz), 1.85-1.89 (1H, m), 2.40(3H, s), 3.51-3.56(2H, m), 3.70-3.75(1H, m), 4.92(1H, d, J=8.8Hz), 5.19(1H, d, J=12.7Hz), 5.22(1H, d, J=12.7Hz), 6.85(1H, br-s), 6.91(1H, dd, J=1.7Hz, 3.4Hz), 7.01(1H, dd, J=1.7Hz, 3.4Hz), 7.21-7.24(3H, m), 7.66 (2H, d, J=8.1Hz). 1183 ¹HNMR(CDCl₃, ppm): 0.19-0.23(2H, m), 0.45-0.50(2H, m), 1.01(6H, t, J=7.1Hz), 1.86-1.93(1H, m), 3.48-3.64(2H, m), 3.67-3.75(1H, m), 3.85(2H, d, J=7.3Hz), 4.87(1H, d, J=9.0Hz), 6.96(1H, br-s), 7.23(2H, d, J=8.5Hz), 7.69(2H, d, J=8.5Hz). 1186 ¹HNMR(CDCl₃, ppm): 0.19-0.23(2H, m), 0.45-0.49(2H, m), 1.01(6H, t, J=7.1Hz), 1.86-1.93(1H, m), 2.38(3H, s), 3.48-3.62(2H, m), 3.67-3.75(1H, m), 3.84 (2H, d, J=7.3Hz), 4.86(1H, d, J=9.0Hz), 6.96(1H, br-s), 7.21(2H, d, J=8.5Hz), 7.68(2H, d, J=8.5Hz). 1198 ¹HNMR(CDCl₃, ppm): 0.86(9H, s), 1.03(6H, t, J=5.6Hz), 1.86-1.90(1H, m), 3.48-3.68(2H, m), 3.70-3.75(3H, m), 4.84(1H, d, J=8.5Hz), 6.92(1H, d, J=6.6Hz), 7.20(2H, d, J=8.1Hz), 7.65(2H, d, J=8.1Hz). 1201 ¹HNMR(CDCl₃, ppm): 0.86(9H, s), 1.01(6H, t, J=5.6Hz), 1.86-1.91(1H, m), 2.39(3H, s), 3.48-3.68(2H, m), 3.70-3.76(3H, m), 4.84(1H, d, J=8.5Hz), 6.94 (1H, d, J=6.6Hz), 7.22(2H, d, J=8.1Hz), 7.67(2H, d, J=8.1Hz). 1213 ¹HNMR(CDCl₃, ppm): 1.03(6H, t, J=7.1Hz), 1.68(3H, s), 1.84-1.90(1H, m), 3.46-3.75(3H, m), 4.45(2H, s), 4.83(1H, s), 4.90-4.95(2H, m), 6.87(1H, br-s), 7.22(2H, d, J=8.1Hz), 7.68(2H, d, J=8.1Hz). 1216 ¹HNMR(CDCl₃, ppm): 1.01(6H, t, J=7.1Hz), 1.67(3H, s), 1.84-1.90(1H, m), 2.39(3H, s), 3.46-3.75(3H, m), 4.44(2H, s), 4.83(1H, s), 4.90-4.94(2H, m), 6.87 (1H, br-s), 7.21(2H, d, J=8.1Hz), 7.67(2H, d, J=8.1Hz). 1228 ¹HNMR(CDCl₃, ppm): 0.75(3H, d, J=6.6Hz), 0.90(3H, d, J=6.6Hz), 1.01(6H + 3H×1/2, t, J=6.6Hz), 1.13(3H×1/2, d, J=6.6Hz), 1.82-1.91(1H, m), 3.45-3.65 (2H, m), 3.69-3.77(1H, m), 4.56-4.61(1H, m), 4.75(1H, t, J=8.1Hz), 6.94(1H, d, J=9.0Hz), 7.20-7.24(2H, m), 7.66(2H, t, J=7.6Hz). 1231 ¹HNMR(CDCl₃, ppm): 0.75(3H, d, J=6.6Hz), 0.89(3H, d, J=6.6Hz), 1.01(6H + 3H×1/2, t, J=6.6Hz), 1.14(3H×1/2, d, J=6.6Hz), 1.82-1.91(1H, m), 2.38(3H, s), 3.45-3.65(2H, m), 3.69-3.76(1H, m), 4.56-4.62(1H, m), 4.75(1H, t, J=8.1Hz), 6.95(1H, d, J=9.0Hz), 7.20-7.23(2H, m), 7.68(2H, t, J=7.6Hz). 1258 ¹HNMR(CDCl₃, ppm): 1.00(6H, t, J=7.6Hz), 1.86-1.92(1H, m), 2.05(3H, s), 2.62(2H, t, J=6.8Hz), 3.47-3.73(3H, m), 4.15-4.24(2H, m), 4.89(1H, d, J=8.5Hz), 6.84(1H, br-s), 7.22(2H, d, J=8.1Hz), 7.67(2H, d, J=8.1Hz). 1261 ¹HNMR(CDCl₃, ppm): 1.00(6H, t, J=7.6Hz), 1.86-1.91(1H, m), 2.07(3H, s), 2.39(3H, s), 2.62(2H, t, J=6.8Hz), 3.47-3.72(3H, m), 4.15-4.23(2H, m), 4.89 (1H, d, J=8.5Hz), 6.81(1H, br-s), 7.23(2H, d, J=8.1Hz), 7.68(2H, d, J=8.1Hz). 1273 ¹HNMR(CDCl₃, ppm): 0.98(3H, d, J=6.8Hz), 1.02(3H, d, J=6.8Hz), 1.83-1.90 (1H, m), 2.40(3H, s), 3.13-3.18(2H, m), 3.41-3.45(1H, m), 3.66-3.70(2H, m), 4.34-4.40(1H, m), 4.49-4.54(1H, m), 5.20(1H, d, J=8.1Hz), 6.64(1H, br-s), 7.26 (2H, d, J=7.8Hz), 7.65(2H, d, J=7.8Hz). 1276 ¹HNMR(CDCl₃, ppm): 0.99(3H, d, J=6.8Hz), 1.01(3H, d, J=6.8Hz), 1.83-1.90 (1H, m), 2.40(3H, s), 2.81(3H, s), 3.13-3.16(2H, m), 3.41-3.45(1H, m), 3.66-3.70(2H, m), 4.34-4.40(1H, m), 4.49-4.55(1H, m), 5.19(1H, d, J=8.1Hz), 6.66(1H, br-s), 7.24(2H, d, J=7.8Hz), 7.66(2H, d, J=7.8Hz).

Examples of Formulations and Tests

The examples of the formulations and the activity tests of the fungicides according to the invention will be shown below. In the following examples, the term “part” hereinafter used means “part by weight” or “% by weight”.

Example of Formulation 1 Granules

Thirty parts of the compound of the invention (30), 22 parts of bentonite, 45 parts of talc, 3 parts of Sorpol 5060 (surfactant: Toho Chemical Industry Co., Ltd., brand name) and a small quantity of antifoamer were kneaded uniformly, granulated with a basket granulating machine, and dried to obtain 100 parts of granules.

Example of Formulation 2 Granules

Fifteen parts of the compound of the invention (241), 60 parts of bentonite, 21 parts of talc, 1 part of sodium dodecylbenzenesulfonate, 1 part of polyoxyethylenealkyl allyl ether and 2 parts of sodium ligninsulfonate were mixed, kneaded uniformly with the addition of a suitable quantity of water, granulated with a basket granulating machine, and dried to obtain 100 parts of granules.

Example of Formulation 3 Wettable Powder

Fifty parts of the compound of the invention (290), 40 parts of calcium carbonate, 5 parts of Sorpol 5039 (a mixture of anionic surfactant and white carbon: Toho Chemical Industry Co., Ltd., brand name) and 5 parts of white carbon were mixed and milled uniformly to obtain a wettable powder.

Example of Formulation 4 Wettable Powder

Thirty parts of the compound of the invention (526), 63 parts of kaolinite, 5 parts of Sorpol 5039 (a mixture of anionic surfactant and white carbon: Toho Chemical Industry Co., Ltd., brand name) and 2 parts of white carbon were mixed and milled uniformly to obtain wettable powder.

Example of Formulation 5 Emulsion

Twenty parts of the compound of the invention (674), 55 parts of xylene, 20 parts of N,N-dimethylformamide and 5 parts of Sorpol 2680 (surfactant) were mixed uniformly to obtain an emulsion concentrate.

Example of Formulation 6 Flowable

Of all the ingredients of 40 parts of the compound of the invention (742), 5 parts of Sorpol 3353 (a nonionic surfactant: Toho Chemical Industry Co., Ltd., brand name), 5 parts of 1% aqueous solution of xanthan gum, 40 parts of water and 10 parts of ethylene glycol, those except the active ingredient were dissolved uniformly, and then the compound of the invention was added. After fully stirred, the mixture was wet milled with a sand mill to obtain a flowable.

Example of Formulation 7 Powder

Five parts of the compound of the invention (807) and 95 parts of clay were admixed to obtain powder.

Test Example 1 Test of Rice Blast Controlling Effect (Spray Application Test)

A diluted solution of a wettable powder prepared at 500 ppm in accordance with formulation Example 4 was applied to a rice pot (variety: Koshihikari; 2-leaf stage) and air-dried. The plant was put into an artificial weather room (set conditions: 22° C., 12-hour dark light cycle) and spray-inoculated with a suspension of Pyricularia oryzae spores. The artificial weather room was kept at high humidity, and the plant was examined after 7 days. The preventive value was calculated by the following equation and the controlling effect was evaluated based on the criteria shown in the following table. The results are shown in Table 3. Preventive value (%)=(1−the number of lesions in treated plot/the number of lesions in untreated plot)×100 Effect Preventive value A 100% B 80% or more and less than 100% C 50% or more and less than 80% D less than 50%

As a control, the following chemicals were used.

TABLE 3 Rice blast controlling effect test (Spray Application Test) Comp. No. Grade of Effect 4 A 26 A 30 A 66 A 215 A 216 A 236 A 237 A 238 A 239 A 240 A 241 A 242 A 243 A 245 A 246 A 247 A 279 A 284 A 289 A 290 A 384 A 387 A 464 B 469 B 470 A 471 A 504 B 526 A 530 A 596 A 600 A 636 A 674 A 677 A 739 A 742 A 804 A 807 A 1049 A 1050 A 1063 A 1066 A 1078 A 1081 A 1123 A 1126 A 1138 A 1141 A 1153 A 1156 A 1168 A 1171 A 1183 A 1186 A 1198 A 1201 A 1213 A 1216 A 1228 A 1231 A 1258 A 1261 A 1273 A 1276 A Formula (7) D Formula (8) D

Test Example 2 Test of Rice Blast Controlling Effect (Water Surface Application)

Rice seedlings (variety: Koshihikari; 3-leaf stage) were planted in 1/5000 are Wagner pots and grown for one week in a green house. Granules prepared in accordance with Formulation Example 2 were applied to water surface in each pot at a rate of 3 kg/10 ares. After 30 days from the application, a liquid suspension of Pyricularia oryzae spores was directly sprayed to the rice plants. The rice plants were placed under the conditions of 25° C. and high humidity for 1 week, and the number of lesions was checked. The preventive value was calculated by the following equation and the controlling effect was evaluated based on the following standard. The results are shown in Table 4. As a control, the same chemical as in Test Example 1 was used. Preventive value (%)=(1−the number of lesions in treated plot/the number of lesions in untreated plot)×100 Effect Preventive value A From 80% to 100% B 50% or more and less than 80% C less than 50%

TABLE 4 Rice blast controlling effect test (Water surface application) Comp. No. Grade of Effect 4 A 26 A 30 A 66 A 215 A 216 A 236 A 237 A 238 A 239 A 240 A 241 A 242 A 243 A 245 A 246 A 247 A 279 A 284 A 289 A 290 A 384 A 387 A 464 B 469 B 470 A 471 A 504 B 526 A 530 A 596 A 600 A 636 A 674 A 677 A 739 A 742 A 804 A 807 A 1049 A 1050 A 1063 A 1066 A 1078 A 1081 A 1123 A 1126 A 1138 A 1141 A 1153 A 1156 A 1168 A 1171 A 1183 A 1186 A 1198 A 1201 A 1213 A 1216 A 1228 A 1231 A 1258 A 1261 A 1273 A 1276 A Formula (7) C Formula (8) C

Test Example 3 Test of Rice Blast Controlling Effect (Nursery Box Treatment)

Rice seedlings (variety: Koshihikari; 2-leaf stage) raised in a nursery box for rice (30 cm×60 cm×3 cm) were treated with granules prepared in accordance with Formulation Example 1 in a quantity of 50 g per box. After 3 days, the rice seedlings were transplanted into a 1/5000 are Wagner in area and raised in a greenhouse. Thirty days after the transplantation, the plant was spray-inoculated with a suspension of Pyricularia oryzae spores, allowed to keep under the conditions of 25° C. and high humidity for 1 week, and the number of lesions was counted. The preventive value was calculated by the following equation and the controlling effect was evaluated based on the same criteria as in Test Example 2. The results are shown in Table 5. As a control, the same chemical as in Test Example 1 was used. Preventive value (%)=(1−the number of lesions in treated plot/the number of lesions in untreated plot)×100

TABLE 5 Test of rice blast controlling effect (Nursery box treatment) Comp. No. Grade of Effect 4 A 26 A 30 A 66 A 215 A 216 A 236 A 237 A 238 A 239 A 240 A 241 A 242 A 243 A 245 A 246 A 247 A 279 A 284 A 289 A 290 A 384 A 387 A 464 B 469 B 470 A 471 A 504 B 526 A 530 A 596 A 600 A 636 A 674 A 677 A 739 A 742 A 804 A 807 A 1049 A 1050 A 1063 A 1066 A 1078 A 1081 A 1123 A 1126 A 1138 A 1141 A 1153 A 1156 A 1168 A 1171 A 1183 A 1186 A 1198 A 1201 A 1213 A 1216 A 1228 A 1231 A 1258 A 1261 A 1273 A 1276 A Formula (7) C Formula (8) C

INDUSTRIAL APPLICABILITY

The diamine derivative according to this invention exhibit an excellent rice blast controlling effect, but, on the other hand, does not injure useful crops; therefore, it is very useful as an agricultural and horticultural fungicide. 

1. A diamine derivative, represented by the following general formula (1):

wherein R1 represents an alkyl group with 1 to 6 carbon atoms provided that the case is excluded where R1 is a tert-butyl, a cycloalkyl group with 3 to 6 carbon atoms, an alkenyl group with 2 to 6 carbon atoms, a cycloalkenyl group with 3 to 6 carbon atoms, an alkynyl group with 2 to 6 carbon atoms, an arylalkyl group which may be substituted, a heteroarylalkyl group which may be substituted, an aryl group which may be substituted, or a heteroaryl group which may be substituted; R2 and R7 independently represent a hydrogen atom, an alkyl group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 6 carbon atoms, an alkenyl group with 2 to 6 carbon atoms, a cycloalkenyl group with 3 to 6 carbon atoms, an alkynyl group with 2 to 6 carbon atoms, an arylalkyl group which may be substituted, an aryl group which may be substituted, or an acyl group; R3 and R4 independently represent a hydrogen atom, an alkyl group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 6 carbon atoms, an alkenyl group with 2 to 6 carbon atoms, a cycloalkenyl group with 3 to 6 carbon atoms, an alkynyl group with 2 to 6 carbon atoms, an arylalkyl group which may be substituted, a heteroarylalkyl group which may be substituted, an aryl group which may be substituted or a heteroaryl group which may be substituted, or a cycloalkyl group with 3 to 6 carbon atoms including an attached carbon atom; R5 and R6 independently represent a hydrogen atom, an alkyl group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 6 carbon atoms, an alkenyl group with 2 to 6 carbon atoms, a cycloalkenyl group with 3 to 6 carbon atoms, an alkynyl group with 2 to 6 carbon atoms, an arylalkyl group which may be substituted, or an aryl group which may be substituted; provided that the case is excluded where R3, R4, R5 and R6 all represent a hydrogen atom or where any one of R3, R4, R5 and R6 represents a methyl group which may be substituted and the others represent a hydrogen atom, and R8 represents an aryl group which may be substituted or a heteroaryl group which may be substituted.
 2. The diamine derivative according to claim 1, wherein R1 represents an alkyl group with 1 to 6 carbon atoms provided that the case is excluded where R1 is a tert-butyl, a cycloalkyl group with 3 to 6 carbon atoms, an alkenyl group with 2 to 6 carbon atoms, an arylalkyl group which may be substituted, a heteroarylalkyl group which may be substituted, an aryl group which may be substituted, or a heteroaryl group which may be substituted; R2 and R7 independently represent a hydrogen atom, an alkyl group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 6 carbon atoms, an arylalkyl group which may be substituted, an aryl group which may be substituted, or an acyl group; R3 and R4 independently represent a hydrogen atom, an alkyl group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 6 carbon atoms, an alkenyl group with 2 to 6 carbon atoms, an arylalkyl group which may be substituted, a heteroarylalkyl group which may be substituted, an aryl group which may be substituted or a heteroaryl group which may be substituted, or a cycloalkyl group with 3 to 6 carbon atoms including an attached carbon atom; and R5 and R6 independently represent a hydrogen atom, an alkyl group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 6 carbon atoms, an arylalkyl group which may be substituted, or an aryl group which may be substituted; provided that the case is excluded where R3, R4, R5 and R6 all represent a hydrogen atom or where any one of R3, R4, R5 and R6 represents a methyl group which may be substituted and the others represent a hydrogen atom.
 3. The diamine derivative according to claim 2, wherein R2 and R7 independently represent a hydrogen atom, an alkyl group with 1 to 6 carbon atoms, or an acyl group; R3 and R4 independently represent a hydrogen atom, an alkyl group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 6 carbon atoms, an arylalkyl group which may be substituted, an aryl group which may be substituted, or a cycloalkyl group with 3 to 6 carbon atoms including an attached carbon atom; and R5 and R6 independently represent a hydrogen atom, an alkyl group with 1 to 6 carbon atoms, an arylalkyl group which may be substituted, or an aryl group which may be substituted; provided that the case is excluded where R3, R4, R5 and R6 all represent a hydrogen atom or where any one of R3, R4, R5 and R6 represents a methyl group which may be substituted and the others represent a hydrogen atom.
 4. The diamine derivative according to claim 3, wherein R2 and R7 represent a hydrogen atom.
 5. A diamine derivative, represented by the following general formula (9):

wherein R9 represents an alkyl group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 6 carbon atoms, an alkenyl group with 2 to 6 carbon atoms, a cycloalkenyl group with 3 to 6 carbon atoms, an alkynyl group with 2 to 6 carbon atoms, an arylalkyl group which may be substituted, a heteroarylalkyl group which may be substituted, a phenyl group, a phenyl group which is substituted at the fourth position, or a heteroaryl group which may be substituted; R10 and R15 independently represent a hydrogen atom, an alkyl group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 6 carbon atoms, an alkenyl group with 2 to 6 carbon atoms, a cycloalkenyl group with 3 to 6 carbon atoms, an alkynyl group with 2 to 6 carbon atoms, an arylalkyl group which may be substituted, an aryl group which may be substituted, or an acyl group; One of R11 and R12 represents a methyl group, and the other represents a hydrogen atom; R13 and R14 represent a hydrogen atom, respectively; and R16 represents a phenyl group, a phenyl group which is substituted at the fourth position, or a heteroaryl group which may be substituted.
 6. The diamine derivative according to claim 5, wherein R9 represents an alkyl group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 6 carbon atoms, an alkenyl group with 2 to 6 carbon atoms, an arylalkyl group which may be substituted, a heteroarylalkyl group which may be substituted, a phenyl group, a phenyl group which is substituted at the fourth position, or a heteroaryl group which may be substituted; and R10 and R15 represent a hydrogen atom, an alkyl group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 6 carbon atoms, an arylalkyl group which may be substituted, an aryl group which may be substituted, or an acyl group, independently.
 7. The diamine derivative according to claim 6, wherein R10 and R15 independently represent a hydrogen atom, an alkyl group with 1 to 6 carbon atoms, or an acyl group.
 8. The diamine derivative according to claim 7, wherein at R10 and R15 represent a hydrogen atom, respectively.
 9. A fungicide, wherein it contains the diamine derivative according to claim 8 as an active ingredient.
 10. A process for producing the diamine derivative according to claim 1, wherein a compound having the following general formula (2):

wherein R1, R2, R3, R4, R5, R6 and R7 represent the same groups as those of the compounds according to claim 1, is reacted with a compound having the following general formula (3):

wherein R8 represents the same group as that of the compound according to claim 1, and X represents a leaving group.
 11. A process for producing the diamine derivative according to claim 1, wherein a compound of the general formula (2) is condensed with a compound having the following general formula (4):

wherein R8 represents the same group as that of the compounds according to claim
 1. 12. A process for producing the diamine derivative according to claim 1, wherein a compound having the following general formula (5):

wherein R2, R3, R4, R5, R6, R7 and R8 represent the same groups as those of the compound according to claim 1, is reacted with a compound having the following general formula (6):

wherein R1 represents the same group as that of the compound according to claim 1, and X represents a leaving group.
 13. A process for producing the diamine derivative according to claim 5, wherein a compound having the following general formula (10):

wherein R9, R10, R11, R12, R13, R14 and R15 represent the same groups as those of the compounds according to claim 5, is reacted with a compound having the following general formula (11):

wherein R16 represents the same group as that of the compound according to claim 5, and X represents a leaving group.
 14. A process for producing the diamine derivative according to claim 5, wherein a compound of the general formula (10) is condensed with a compound having the following general formula (12):

wherein R16 represents the same group as that of the compounds according to claim
 5. 15. A process for producing the diamine derivative according to claim 5, wherein a compound having the following general formula (13):

wherein R10, R11, R12, R13, R14, R15 and R16represent the same groups as those of the compound according to claim 5, is reacted with a compound having the following general formula (14):

wherein R9 represents the same group as that of the compound according to claim 5, and X represents a leaving group.
 16. A fungicide, wherein it contains the diamine derivative according to claim 1 as an active ingredient.
 17. A fungicide, wherein it contains the diamine derivative according to claim 5 as an active ingredient. 